WO2017057253A1 - 処理液及びパターン形成方法 - Google Patents
処理液及びパターン形成方法 Download PDFInfo
- Publication number
- WO2017057253A1 WO2017057253A1 PCT/JP2016/078230 JP2016078230W WO2017057253A1 WO 2017057253 A1 WO2017057253 A1 WO 2017057253A1 JP 2016078230 W JP2016078230 W JP 2016078230W WO 2017057253 A1 WO2017057253 A1 WO 2017057253A1
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- WIPO (PCT)
- Prior art keywords
- group
- solvent
- acetate
- examples
- organic solvent
- Prior art date
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- 239000007788 liquid Substances 0.000 title claims abstract description 143
- 238000000034 method Methods 0.000 title claims abstract description 114
- 230000007261 regionalization Effects 0.000 title claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 139
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 230000005855 radiation Effects 0.000 claims abstract description 68
- 238000000059 patterning Methods 0.000 claims abstract description 12
- 238000005406 washing Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims description 203
- 125000004432 carbon atom Chemical group C* 0.000 claims description 139
- 238000012545 processing Methods 0.000 claims description 56
- 238000011161 development Methods 0.000 claims description 38
- 230000018109 developmental process Effects 0.000 claims description 38
- 239000004215 Carbon black (E152) Substances 0.000 claims description 33
- 229930195733 hydrocarbon Natural products 0.000 claims description 33
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 32
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 31
- 150000002430 hydrocarbons Chemical class 0.000 claims description 31
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 24
- 150000002576 ketones Chemical class 0.000 claims description 20
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 16
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 claims description 13
- 229940117955 isoamyl acetate Drugs 0.000 claims description 13
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 10
- 238000004140 cleaning Methods 0.000 claims description 8
- NKIZSFXAIKPBCL-UHFFFAOYSA-N 2,5-dichloro-3,6-dimethylpyrazine Chemical compound CC1=NC(Cl)=C(C)N=C1Cl NKIZSFXAIKPBCL-UHFFFAOYSA-N 0.000 claims description 7
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 claims description 7
- BGYICJVBGZQOCY-UHFFFAOYSA-N heptyl propanoate Chemical compound CCCCCCCOC(=O)CC BGYICJVBGZQOCY-UHFFFAOYSA-N 0.000 claims description 7
- GQKZRWSUJHVIPE-UHFFFAOYSA-N sec-amyl acetate Natural products CCCC(C)OC(C)=O GQKZRWSUJHVIPE-UHFFFAOYSA-N 0.000 claims description 7
- XHIUFYZDQBSEMF-UHFFFAOYSA-N 2-methylbutyl acetate Chemical compound CCC(C)COC(C)=O XHIUFYZDQBSEMF-UHFFFAOYSA-N 0.000 claims description 6
- 229940072049 amyl acetate Drugs 0.000 claims description 6
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 6
- GOKKOFHHJFGZHW-UHFFFAOYSA-N hexyl propanoate Chemical compound CCCCCCOC(=O)CC GOKKOFHHJFGZHW-UHFFFAOYSA-N 0.000 claims description 6
- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 claims description 6
- 229940043232 butyl acetate Drugs 0.000 claims description 5
- 150000003998 acyclic ketones Chemical class 0.000 claims description 4
- JSLCOZYBKYHZNL-UHFFFAOYSA-N butylisobutyrate Chemical compound CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 230000007547 defect Effects 0.000 abstract description 13
- -1 diacetyl alcohol Chemical compound 0.000 description 158
- 229920005989 resin Polymers 0.000 description 124
- 239000011347 resin Substances 0.000 description 124
- 125000000217 alkyl group Chemical group 0.000 description 115
- 150000001875 compounds Chemical class 0.000 description 72
- 239000000243 solution Substances 0.000 description 69
- 125000003118 aryl group Chemical group 0.000 description 63
- 239000010410 layer Substances 0.000 description 63
- 125000000753 cycloalkyl group Chemical group 0.000 description 61
- 125000001153 fluoro group Chemical group F* 0.000 description 51
- 229910052731 fluorine Inorganic materials 0.000 description 50
- 239000002253 acid Substances 0.000 description 48
- 125000001424 substituent group Chemical group 0.000 description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 40
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 32
- 125000005843 halogen group Chemical group 0.000 description 28
- 229910052710 silicon Inorganic materials 0.000 description 28
- 125000003545 alkoxy group Chemical group 0.000 description 26
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 26
- 238000010894 electron beam technology Methods 0.000 description 26
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 25
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 25
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 24
- 238000010438 heat treatment Methods 0.000 description 24
- 230000002209 hydrophobic effect Effects 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 239000004094 surface-active agent Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 125000002947 alkylene group Chemical group 0.000 description 23
- 150000007514 bases Chemical class 0.000 description 23
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 22
- 239000004210 ether based solvent Substances 0.000 description 22
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 21
- 230000000694 effects Effects 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 description 21
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 19
- 125000004093 cyano group Chemical group *C#N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000000576 coating method Methods 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 16
- 238000011156 evaluation Methods 0.000 description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 description 16
- 238000007654 immersion Methods 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- 230000009471 action Effects 0.000 description 15
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical group CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 15
- 125000005647 linker group Chemical group 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 150000001450 anions Chemical class 0.000 description 14
- 239000003963 antioxidant agent Substances 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 239000003759 ester based solvent Substances 0.000 description 14
- 239000012487 rinsing solution Substances 0.000 description 14
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 13
- 125000005842 heteroatom Chemical group 0.000 description 13
- 125000002950 monocyclic group Chemical group 0.000 description 13
- 125000000962 organic group Chemical group 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 125000002252 acyl group Chemical group 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000002608 ionic liquid Substances 0.000 description 12
- 150000002596 lactones Chemical group 0.000 description 12
- 230000002265 prevention Effects 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 11
- 239000005453 ketone based solvent Substances 0.000 description 11
- 239000012046 mixed solvent Substances 0.000 description 11
- 125000001624 naphthyl group Chemical group 0.000 description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 11
- 239000010703 silicon Substances 0.000 description 11
- 238000003860 storage Methods 0.000 description 11
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 11
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 10
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- 229940116333 ethyl lactate Drugs 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- 239000011342 resin composition Substances 0.000 description 10
- SGVYKUFIHHTIFL-UHFFFAOYSA-N 2-methylnonane Chemical compound CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 239000005456 alcohol based solvent Substances 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000005702 oxyalkylene group Chemical group 0.000 description 9
- 230000036961 partial effect Effects 0.000 description 9
- 125000003367 polycyclic group Chemical group 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 8
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 8
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 8
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 230000000269 nucleophilic effect Effects 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 230000008961 swelling Effects 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 6
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 6
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 6
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 6
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- IYTXKIXETAELAV-UHFFFAOYSA-N Aethyl-n-hexyl-keton Natural products CCCCCCC(=O)CC IYTXKIXETAELAV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 6
- 239000003463 adsorbent Substances 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 6
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 6
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 125000006353 oxyethylene group Chemical group 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 239000002344 surface layer Substances 0.000 description 6
- BJFHJALOWQJJSQ-UHFFFAOYSA-N (3-methoxy-3-methylpentyl) acetate Chemical compound CCC(C)(OC)CCOC(C)=O BJFHJALOWQJJSQ-UHFFFAOYSA-N 0.000 description 5
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 5
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 5
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 5
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
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Classifications
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5022—Organic solvents containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5027—Hydrocarbons
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
- G03F7/0043—Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting
Definitions
- the present invention relates to a processing liquid for patterning a resist film and a pattern forming method. More specifically, the present invention is used in a semiconductor manufacturing process such as an IC (Integrated Circuit), a circuit board such as a liquid crystal and a thermal head, and a lithography process for other photofabrication.
- the present invention relates to a processing liquid and a pattern forming method.
- Patent Document 1 discloses that an organic processing solution containing a mixture of a first organic solvent and a second organic solvent selected from a ketone solvent and an ester solvent is used as a developing solution. .
- the developing solution and the rinsing solution are not limited to the types of patterns such as the L / S pattern and the C / H pattern, and are required to exhibit good performance, and the developing solution that can simultaneously eliminate the occurrence of pattern collapse and omission defects. And a rinse solution was sought.
- the present invention has been made in view of the above points, and a processing liquid and a pattern for resist film patterning that can simultaneously suppress the occurrence of pattern collapse in a resist L / S pattern and the occurrence of missing defects in a resist C / H pattern.
- An object is to provide a forming method.
- the present inventors have used an organic processing liquid containing a combination of at least two organic solvents having different solubility parameters (hereinafter also referred to as “SP values”), It has been found that the desired effect can be obtained. More specifically, the present inventors have found that the above object can be achieved by the following configuration.
- a processing solution for patterning a resist film which is used to perform at least one of development and washing on a resist film obtained from an actinic ray-sensitive or radiation-sensitive composition, and contains an organic solvent, SP value first organic solvent and the SP value of 16.3MPa 1/2 or less contains a second organic solvent of 17.1MPa 1/2 or more, the processing solution.
- the processing liquid according to (1), wherein the processing liquid is a rinsing liquid.
- the ester solvent is butyl acetate, amyl acetate, isoamyl acetate, 2-methylbutyl acetate, 1-methylbutyl acetate, hexyl acetate, pentyl propionate, hexyl propionate, heptyl propionate, butyl butanoate, and isobutanoic acid.
- a processing liquid for patterning a resist film and a pattern forming method capable of simultaneously suppressing the occurrence of pattern collapse in the resist L / S pattern and the occurrence of defective omission in the resist C / H pattern.
- the treatment liquid of the present invention is a treatment liquid for resist film patterning that contains an organic solvent and is used for performing at least one of development and washing on a resist film obtained from an actinic ray-sensitive or radiation-sensitive composition. is there.
- Treatment solution of the present invention includes a first organic solvent SP value of 16.3MPa 1/2 or less, SP value and a second organic solvent of 17.1MPa 1/2 or more, the. According to the processing liquid of the present invention, the occurrence of pattern collapse in the resist L / S pattern and the occurrence of defective omission in the resist C / H pattern can be suppressed at the same time. Although the details of this reason have not yet been clarified, it is assumed as follows.
- missing defects in the C / H pattern are problems that are particularly easily manifested by organic solvent development. That is, due to the effect of PAG (photoacid generator) segregated on the surface, the amount of deprotection is slightly larger than that of the bulk layer, and the surface layer of the relatively high polarity resist film has insufficient dissolution contrast in organic solvent development. This is considered to be caused without being completely dissolved.
- the treatment liquid of the present invention can penetrate through the surface layer of the relatively highly polar resist film described above.
- the processing solution used as the developing solution and / or the rinsing solution contains at least two kinds of organic solvents having different SP values, thereby causing pattern collapse in the resist L / S pattern and resist C. The occurrence of omission defects in the / H pattern can be suppressed at the same time.
- the SP value of the present invention is calculated using the Fedors method described in “Properties of Polymers, 2nd edition, 1976 publication”.
- the unit of SP value is MPa 1/2 unless otherwise specified.
- the processing solution of the present invention is usually used as a developing solution and / or a rinsing solution.
- the treatment liquid preferably contains an organic solvent, and further contains an antioxidant and / or a surfactant.
- the organic solvent will be described first, and then the antioxidant and surfactant that may be contained in the treatment liquid will be described.
- SP value includes a first organic solvent 16.3MPa 1/2 or less, SP value and a second organic solvent to 17.1MPa 1/2 or more.
- the SP value of the first organic solvent is larger than 16.3 MPa 1/2 , the affinity for the resist film is too high, and the developer and the rinsing liquid easily penetrate into the resist film pattern. Cause swelling.
- the SP value of the second organic solvent is smaller than 17.1 MPa 1/2 , the solubility of the resist film surface layer having a relatively high polarity relative to the bulk layer described above is insufficient, and the C / H Omission failure occurs.
- the first organic solvent having an SP value of 16.3 MPa 1/2 or less is selected from various organic solvents.
- solvents such as hydrocarbon solvents, ether solvents, and ester solvents may be used. it can.
- the minimum of SP value of a 1st organic solvent is not specifically limited, For example, it is 14.5 Mpa1 / 2 or more.
- SP value of 16.3MPa 1/2 or less of the hydrocarbon-based solvent, or an ether solvent are preferred, SP value of 16.3MPa 1/2 or less of the hydrocarbon-based solvents are more preferable.
- the SP value of the first organic solvent is preferably 16.0 MPa 1/2 or less, and more preferably in the range of 15.0 to 16.0 MPa 1/2 . By setting the SP value within this range, it is possible to improve the C / H omission failure. From the viewpoint of further improving the effect of simultaneously suppressing the occurrence of pattern collapse in the resist L / S pattern and the occurrence of defective defects in the resist C / H pattern (hereinafter also referred to as “effects of the present invention”).
- the first organic solvent having an SP value of 16.3 MPa 1/2 or less preferably has a relative dielectric constant of 4.0 or less, preferably 3.0 or less, and more preferably 2.5 or less. "Relative permittivity" is described in "Handbook of Organic Solvent Properties, Ian M. Smallwood, 1996, Elsevier” and “CRC Handbook of Chemistry and Physics, 96th Edition, William M. Haynes, 2015, CRC Press". The specified dielectric constant (mainly a value at a temperature of 20 ° C.) is used.
- hydrocarbon solvents examples are shown below. The numbers in parentheses indicate SP values. Pentane (14.5), hexane (14.9), heptane (15.2), octane (15.5), nonane (15.7), decane (15.8), undecane (16.0), dodecane (16.1), hexadecane (16.2), 2,2,4-trimethylpentane (14.3), 2,2,3-trimethylhexane (14.6), isohexane (14.4), isoheptane ( 14.8), aliphatic hydrocarbon solvents such as isooctane (15.1), isodecane (15.5), isododecane (14.7), and isohexadecane (15.0); Examples thereof include unsaturated hydrocarbon solvents such as octene (15.6), nonene (15.8), decene (16.0), undecene (16.1), and dodecene (16.2).
- the number of double bonds or triple bonds that the unsaturated hydrocarbon solvent has is not particularly limited, and may be located at any position of the hydrocarbon chain (however, the above value indicates that the first position of the carbon difference is two. The case where it is substituted with a heavy bond is shown). Moreover, when an unsaturated hydrocarbon solvent has a double bond, cis body and trans body may be mixed.
- the aliphatic hydrocarbon solvent which is a hydrocarbon solvent may be a mixture of compounds having the same carbon number and different structures as long as the SP value is within the above range.
- decane when decane is used as the aliphatic hydrocarbon solvent, 2-methylnonane (15.5), 2,2-dimethyloctane (15.2), and 4-ethyl which are compounds having the same carbon number and different structures.
- Octane (15.5) or the like may be contained in the aliphatic hydrocarbon solvent.
- the compounds having the same number of carbon atoms and different structures may include only one kind or plural kinds as described above.
- the upper limit of the carbon number of the said aliphatic hydrocarbon solvent is not specifically limited, For example, 16 or less is mentioned, 14 or less is preferable and 12 or less is more preferable.
- decane (15.8), undecane (16.0), or isodecane (15.5) is preferable, and undecane (16.0) is more preferable.
- ether solvents examples include SP values.
- acyclic aliphatic ether solvents such as dipentyl ether (16.2), dibutyl ether (15.9), and dipropyl ether (15.5); Di-2-ethylhexyl ether (15.9), diisopentyl ether (15.6), diisobutyl ether (15.2), diisopropyl ether (14.6), diisohexyl ether (15.6), ethyl iso Pentyl ether (15.4), propyl isopentyl ether (15.6), methyl isobutyl ether (14.7), ethyl isobutyl ether (15.1), propyl isobutyl ether (15.4), and ethyl isopropyl ether ( And acyclic aliphatic ether solvents having a branched alkyl group such as 14.7). Particularly preferred is diisobutaned alkyl group such as 14.7)
- the treatment liquid of the present invention preferably contains a hydrocarbon solvent having 10 or more carbon atoms as the first organic solvent, and includes undecane (16.0) from the viewpoint of further improving the effects of the present invention. It is more preferable.
- the second organic solvent having an SP value of 17.1 MPa 1/2 or more is selected from various organic solvents.
- hydrocarbon solvents can be used.
- the upper limit of SP value of a 2nd organic solvent is not specifically limited, For example, it is 27.0 MPa1 / 2 or less.
- SP value of 17.1MPa 1/2 or more ketone solvents, or ester solvents are preferable, SP value is more preferably 17.1MPa 1/2 or more ketone solvent.
- SP value of the second organic solvent is preferably 17.1 ⁇ 23.0MPa 1/2, more preferably from 17.1 ⁇ 20.0 MPa 1/2, is 17.1 ⁇ 18.1MPa 1/2 Further preferred.
- the second organic solvent of the SP value is 17.1MPa 1/2 or more, preferably a dielectric constant of 6.0 or more, 6 or more It is preferably 20 or less, more preferably 6 or more and 14 or less, and still more preferably 6 or more and 10 or less.
- the ester solvent is a solvent having an ester group in the molecule
- the ketone solvent is a solvent having a ketone group in the molecule
- the alcohol solvent is in the molecule.
- It is a solvent having an alcoholic hydroxyl group
- an amide solvent is a solvent having an amide group in the molecule
- an ether solvent is a solvent having an ether bond in the molecule.
- diethylene glycol monomethyl ether corresponds to both alcohol solvents and ether solvents in the above classification.
- organic solvents that can be used as the second organic solvent are exemplified, but the present invention is not limited thereto.
- the numbers in parentheses indicate SP values.
- ester solvent examples include methyl acetate (18.0), ethyl acetate (17.9), butyl acetate (17.8), isobutyl acetate (17.4), amyl acetate (pentyl acetate) (17.8).
- Examples of the ketone solvent include 2-octanone (18.0), 3-octanone (18.0), 4-octanone (18.0), 2-nonanone (18.0), and 3-nonanone (18. 0), 4-nonanone (18.0), 5-nonanone (18.0), acetone (18.6), 2-heptanone (18.1), 3-heptanone (18.1), 4-heptanone ( 18.1), 2-hexanone (18.2), 3-hexanone (18.2), diisobutyl ketone (17.4), diisopentyl ketone (17.4), diisohexyl ketone (17.4) Diisoheptyl ketone (17.4), ethyl isobutyl ketone (17.7), methyl isopentyl ketone (17.7), ethyl isopentyl ketone (17.7), propyl isopentyl ketone (17.7), Propyl isobutyl ketone (17.7), 3-
- acyclic ketone solvents are preferred from the viewpoint of better effects of the present invention, and 2-octanone (18.0), 3-octanone (18.0), 4-octanone (18 0.0), 2-nonanone (18.0), 3-nonanone (18.0), 4-nonanone (18.0), 5-nonanone (18.0), 2-heptanone (18.1), 3 -Heptanone (18.1), 4-heptanone (18.1), diisobutyl ketone (17.4), diisopentyl ketone (17.4), diisohexyl ketone (17.4), or diisoheptyl ketone (17.4) is more preferable, diisobutyl ketone (17.4), diisopentyl ketone (17.4), diisohexyl ketone (17.4), diisoheptyl ketone (17.4), 4-heptanone. ( 8.1), or 5-nonanone (18.0) is more preferable, diisobuty
- alcohol solvents examples include methanol (28.2), ethanol (25.7), 1-propanol (24.2), isopropanol (23.7), 1-butanol (23.2), 2-butanol. (22.7), 3-methyl-1-butanol (22.0), tert-butyl alcohol (22.3), 1-pentanol (22.4), 2-pentanol (22.0), 1 -Hexanol (21.9), 1-heptanol (21.4), 1-octanol (21.0), 1-decanol (20.5), 2-hexanol (21.5), 2-heptanol (21.
- ether solvents include aromatic ether solvents such as anisole (19.2) and phenetole (19.0); tetrahydrofuran (18.4), tetrahydropyran (18.2), and 1,4- Examples thereof include alicyclic ether solvents such as dioxane. Among these, it is preferable to use glycol ether solvents or aromatic ether solvents such as anisole.
- amide solvent examples include N-methyl-2-pyrrolidone (22.2), N, N-dimethylacetamide (18.7), N, N-dimethylpropioamide (18.5), and N, N-dimethylformamide (21.2) and the like can be used.
- hydrocarbon solvent examples include aliphatic hydrocarbon solvents such as cyclohexane (17.5), cycloheptane (17.5), and cyclooctane (17.5); toluene (18.7), xylene (18.6), ethylbenzene (18.5), propylbenzene (18.4), 1-methyl-4-propylbenzene (18.4), diethylbenzene (18.4), and trimethylbenzene (18.6) Aromatic hydrocarbon solvents such as
- the contents of the first organic solvent and the second organic solvent are not particularly limited, but the content of the first organic solvent is usually 10 to 95% by mass with respect to the total mass of the treatment liquid, preferably It is 20 to 95% by mass, more preferably 30 to 80% by mass, and still more preferably 50 to 80% by mass.
- the content of the second organic solvent is usually 5 to 95% by mass, preferably 10 to 70% by mass, and more preferably 10 to 60% by mass with respect to the total mass of the treatment liquid. .
- the mass ratio of the first organic solvent to the second organic solvent is not particularly limited, but is preferably 0.25 to 9, more preferably 0.4 to 3. .
- the treatment liquid of the present invention may contain the following ionic liquid.
- the ionic liquid is not included as an organic solvent (in other words, not included in the first and second organic solvents).
- the ionic liquid include, as a cation, an aromatic ion such as a pyridinium ion or an imidazolium ion, or an aliphatic amine ion such as a trimethylhexylammonium ion, and the anion includes NO 3 ⁇ , Inorganic ion systems such as CH 3 CO 2 ⁇ , BF 6 ⁇ , or PF 6 ⁇ , or fluorine-containing organic anions such as (CF 3 SO 2 ) 2 N ⁇ , CF 3 CO 2 ⁇ , or CF 3 SO 2 — An ionic liquid having ions or the like; a quaternary ammonium salt ionic liquid is preferably used.
- ionic liquids examples include IL-P14 and IL-A2 (manufactured by Guangei Chemical Industry Co., Ltd.); Elegan SS-100 (manufactured by NOF Corporation), which is a quaternary ammonium salt ionic liquid. Etc. An ionic liquid is used individually by 1 type or in combination of 2 or more types.
- the content of the ionic liquid is not particularly limited, but when the ionic liquid is contained, it is preferably 0.5 to 15% by mass with respect to the total mass of the treatment liquid, and 1 to 10% by mass. More preferably, it is 1 to 5% by mass.
- the SP value mentioned above as the organic solvent is first organic solvent and the SP value of 16.3MPa 1/2 less 17.1MPa 1/2 or more second at least one kind of organic solvent It is only necessary to contain them one by one, and a plurality of these may be contained, or an additional component such as an organic solvent other than the above (an organic solvent whose SP value does not satisfy the above range) or an ionic liquid May further be included.
- the treatment liquid may contain water.
- the water content in the rinsing liquid is usually 60% by mass or less, preferably 30% by mass or less, more preferably 10% by mass or less, and most preferably. 5% by mass or less.
- a favorable rinse characteristic can be acquired by making a moisture content into 60 mass% or less.
- the processing solution of the present invention may be used for either a developing solution or a rinsing solution as a cleaning solution, but is preferably used for a rinsing solution.
- the developer is not particularly limited, and the processing solution of the present invention or a developer that can be used in combination with the processing solution of the present invention described later (particularly preferably It is preferable to use an ester solvent.
- the rinsing solution is not particularly limited, and the processing solution of the present invention or a rinsing solution that can be used in combination with the processing solution of the present invention described later is used. It is preferable.
- the organic solvent used for the developing solution shown below and the organic solvent used for the rinsing liquid are the above-mentioned first organic solvent and second organic solvent, respectively, in each liquid selected from the developing liquid and the rinsing liquid. It is also an organic solvent that can be used in combination (an organic solvent whose SP value does not satisfy the above range).
- the developer can be prepared as a solution containing both the first organic solvent and the second organic solvent described above and the organic solvent used in the developer shown below.
- the rinsing liquid can be prepared as a liquid containing both the first organic solvent and the second organic solvent described above and the organic solvent used in the rinsing liquid described below.
- the organic solvent whose SP value is contained in the range mentioned above in other words, the organic solvent whose SP value is 16.3 MPa 1/2 or less, or the SP value is 17.1 MPa 1 / 2 or more organic solvents
- the organic solvent whose SP value is included in the above-described range corresponds to either the first organic solvent or the second organic solvent. That is, when the developing solution and the rinsing solution contain other organic solvents in addition to the first organic solvent and the second organic solvent, the other organic solvent has an SP value in the organic solvent described below. Is selected from organic solvents that do not satisfy the above range.
- the vapor pressure of the organic solvent used in the developer (the vapor pressure as a whole in the case of a mixed solvent) is preferably 5 kPa or less, more preferably 3 kPa or less, and particularly preferably 2 kPa or less at 20 ° C.
- the organic solvent used in the developer various organic solvents are widely used. For example, ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents, etc. A solvent can be used.
- the developer preferably contains at least one solvent selected from a ketone solvent, an ester solvent, an alcohol solvent, and an ether solvent.
- ester solvent examples include methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, propyl acetate, isopropyl acetate, amyl acetate (pentyl acetate), isoamyl acetate (isopentyl acetate, 3-methylbutyl acetate), acetic acid 2 -Methylbutyl, 1-methylbutyl acetate, hexyl acetate, isohexyl acetate, heptyl acetate, octyl acetate, ethyl methoxyacetate, ethyl ethoxyacetate, propylene glycol monomethyl ether acetate (PGMEA; also known as 1-methoxy-2-acetoxypropane), ethylene glycol mono Ethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol
- butyl acetate, amyl acetate, isoamyl acetate, 2-methylbutyl acetate, 1-methylbutyl acetate, hexyl acetate, pentyl propionate, hexyl propionate, heptyl propionate, or butyl butanoate are preferably used, and isoamyl acetate Is particularly preferably used.
- ketone solvents include 1-octanone, 2-octanone, 1-nonanone, 2-nonanone, acetone, 2-heptanone, 4-heptanone, 1-hexanone, 2-hexanone, diisobutyl ketone, cyclohexanone, methylcyclohexanone, Examples include phenylacetone, methyl ethyl ketone, methyl isobutyl ketone, acetylacetone, acetonylacetone, ionone, diacetonyl alcohol, acetylcarbinol, acetophenone, methylnaphthylketone, isophorone, propylene carbonate, and ⁇ -butyrolactone. 2-heptanone is preferred.
- alcohol solvents include methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, 3-methyl-1-butanol, tert-butyl alcohol, 1-pentanol, 2-pentanol, 1 -Hexanol, 1-heptanol, 1-octanol, 1-decanol, 2-hexanol, 2-heptanol, 2-octanol, 3-hexanol, 3-heptanol, 3-octanol, 4-octanol, 3-methyl-3-pen Tanol, cyclopentanol, 2,3-dimethyl-2-butanol, 3,3-dimethyl-2-butanol, 2-methyl-2-pentanol, 2-methyl-3-pentanol, 3-methyl-2- Pentanol, 3-methyl-3-pentanol, 4-methyl- -Pentanol, 4-methyl-3-pentanol,
- ether solvents include glycol ether solvents containing no hydroxyl group, such as propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether.
- examples include aromatic ether solvents such as phenetole; dioxane, tetrahydrofuran, tetrahydropyran, perfluoro-2-butyltetrahydrofuran, perfluorotetrahydrofuran, 1,4-dioxane, and isopropyl ether.
- glycol ether solvents and aromatic ether solvents such as anisole are preferred.
- amide solvents include N-methyl-2-pyrrolidone, N, N-dimethylacetamide, N, N-dimethylformamide, hexamethylphosphoric triamide, and 1,3-dimethyl-2-imidazolidinone. Is mentioned.
- hydrocarbon solvent examples include pentane, hexane, octane, nonane, decane, dodecane, undecane, hexadecane, 2,2,4-trimethylpentane, 2,2,3-trimethylhexane, perfluorohexane, and perfluoro.
- Aliphatic hydrocarbon solvents such as heptane; toluene, xylene, ethylbenzene, propylbenzene, 1-methylpropylbenzene, 2-methylpropylbenzene, dimethylbenzene, diethylbenzene, ethylmethylbenzene, trimethylbenzene, ethyldimethylbenzene, and dipropyl And aromatic hydrocarbon solvents such as benzene.
- an unsaturated hydrocarbon solvent can also be used, and examples thereof include unsaturated hydrocarbon solvents such as octene, nonene, decene, undecene, dodecene, and hexadecene.
- the number of double bonds or triple bonds that the unsaturated hydrocarbon solvent has is not particularly limited, and may be at any position of the hydrocarbon chain. Moreover, when an unsaturated hydrocarbon solvent has a double bond, cis body and trans body may be mixed.
- the aliphatic hydrocarbon solvent that is a hydrocarbon solvent may be a mixture of compounds having the same number of carbon atoms and different structures. For example, when decane is used as the aliphatic hydrocarbon solvent, 2-methylnonane, 2,2-dimethyloctane, 4-ethyloctane, and isooctane, which are compounds having the same carbon number and different structures, are aliphatic hydrocarbon-based. It may be contained in a solvent.
- the compounds having the same number of carbon atoms and different structures may include only one kind or plural kinds as described above.
- the developer has 6 or more carbon atoms (preferably 6 to 14 carbon atoms) from the standpoint that swelling of the resist film can be suppressed when EUV light (Extreme Ultra Violet) and EB (Electron Beam) are used in the exposure process described later. 6 to 12 is more preferable, and 6 to 10 is still more preferable.) It is preferable to use an ester solvent having 2 or less hetero atoms.
- the hetero atom of the ester solvent is an atom other than a carbon atom and a hydrogen atom, and examples thereof include an oxygen atom, a nitrogen atom, and a sulfur atom.
- the number of heteroatoms is preferably 2 or less.
- ester solvents having 6 or more carbon atoms and 2 or less heteroatoms include butyl acetate, amyl acetate, isoamyl acetate, 2-methylbutyl acetate, 1-methylbutyl acetate, hexyl acetate, pentyl propionate, propionic acid It is preferably at least one selected from hexyl, heptyl propionate, butyl butanoate, and butyl isobutanoate, more preferably isoamyl acetate or butyl isobutanoate.
- the developer is replaced with the above ester solvent having 6 or more carbon atoms and 2 or less hetero atoms.
- a mixed solvent of the ester solvent and the hydrocarbon solvent, or a mixed solvent of the ketone solvent and the hydrocarbon solvent may be used. Even in this case, it is effective in suppressing the swelling of the resist film.
- isoamyl acetate is preferably used as the ester solvent.
- hydrocarbon solvent it is preferable to use a saturated hydrocarbon solvent (for example, octane, nonane, decane, dodecane, undecane, and hexadecane) from the viewpoint of adjusting the solubility of the resist film.
- a saturated hydrocarbon solvent for example, octane, nonane, decane, dodecane, undecane, and hexadecane
- ketone solvent examples include 1-octanone, 2-octanone, 1-nonanone, 2-nonanone, acetone, 2-heptanone (methyl amyl ketone), 4-heptanone, 1-hexanone, 2-hexanone, diisobutyl ketone, 2,5-dimethyl-4-hexanone, cyclohexanone, methylcyclohexanone, phenylacetone, methylethylketone, methylisobutylketone, acetylacetone, acetonylacetone, ionone, diacetonyl alcohol, acetylcarbinol, acetophenone, methylnaphthylketone, isophorone, and Examples thereof include propylene carbonate, and diisobutyl ketone and 2,5-dimethyl-4-hexanone are preferably used.
- the content of the hydrocarbon solvent is not particularly limited
- a plurality of the above organic solvents may be mixed, or may be used by mixing with other solvents or water.
- the water content of the developer as a whole is preferably less than 10% by mass, and more preferably substantially free of moisture.
- the concentration of the organic solvent in the developer (total in the case of mixing) is preferably 50% by mass or more, more preferably 85% by mass or more, more preferably 90% by mass or more, and particularly preferably 95% by mass or more. Most preferably, it consists essentially of an organic solvent.
- the case of substantially consisting only of an organic solvent means a case of containing a small amount of components such as a surfactant, an antioxidant, a stabilizer, and an antifoaming agent in addition to the case where the developer is contained at 100% by mass. Shall be included.
- an ester solvent represented by the general formula (S1) or general formula (S2) described later can also be suitably exemplified.
- the ester solvent it is preferable to use a solvent represented by the general formula (S1) among the ester solvents represented by the general formula (S1) or (S2), more preferably an alkyl acetate, More preferred is butyl, amyl acetate (pentyl acetate), or isoamyl acetate (isopentyl acetate).
- R and R ′ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxyl group, an alkoxycarbonyl group, a carboxyl group, a hydroxyl group, a cyano group, or a halogen atom. .
- R and R ′ may be bonded to each other to form a ring.
- the alkyl group, alkoxyl group, and alkoxycarbonyl group for R and R ′ preferably have 1 to 15 carbon atoms, and the cycloalkyl group preferably has 3 to 15 carbon atoms.
- R and R ′ are preferably a hydrogen atom or an alkyl group, and an alkyl group, a cycloalkyl group, an alkoxyl group, an alkoxycarbonyl group, and a ring formed by combining R and R ′ with respect to R and R ′, It may be substituted with a hydroxyl group, a group containing a carbonyl group (for example, an acyl group, an aldehyde group, alkoxycarbonyl, etc.), a cyano group, or the like.
- Examples of the solvent represented by the general formula (S1) include methyl acetate, butyl acetate, ethyl acetate, isopropyl acetate, amyl acetate, isoamyl acetate, methyl formate, ethyl formate, butyl formate, propyl formate, ethyl lactate, and butyl lactate.
- Examples include isopropyl acid, methyl 2-hydroxypropionate, and ethyl 2-hydroxypropionate.
- R and R ′ are unsubstituted alkyl groups.
- the solvent represented by the general formula (S1) is preferably alkyl acetate, more preferably butyl acetate, amyl acetate (pentyl acetate), or isoamyl acetate (isopentyl acetate), and isoamyl acetate. Is more preferable.
- the solvent represented by the general formula (S1) may be used in combination with one or more other organic solvents.
- the combined solvent in this case is not particularly limited as long as it can be mixed without being separated into the solvent represented by the general formula (S1), and the solvents represented by the general formula (S1) may be used in combination.
- the solvent represented by the general formula (S1) is mixed with a solvent selected from other ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents. Also good.
- One or more solvents can be used in combination, but it is preferable to use one solvent in order to obtain stable performance.
- the mixing ratio of the solvent represented by the general formula (S1) and the combined solvent is usually 20:80 to 99: 1, preferably 50:50 to 97: by mass ratio. 3, more preferably 60:40 to 95: 5, and most preferably 60:40 to 90:10.
- a glycol ether solvent As the organic solvent used as the developer, a glycol ether solvent can be used.
- a glycol ether solvent a solvent represented by the following general formula (S2) may be used.
- R ′′ and R ′′ ′′ each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxyl group, an alkoxycarbonyl group, a carboxyl group, a hydroxyl group, a cyano group or a halogen atom.
- R ′′ and R ′′ ′′ may be bonded to each other to form a ring.
- R ′′ and R ′′ ′′ are preferably a hydrogen atom or an alkyl group.
- the alkyl group, alkoxyl group, and alkoxycarbonyl group for R ′′ and R ′′ ′′ preferably have 1 to 15 carbon atoms, and the cycloalkyl group has 3 to 15 carbon atoms.
- R ′ ′′ represents an alkylene group or a cycloalkylene group.
- R ′ ′′ is preferably an alkylene group.
- the number of carbon atoms of the alkylene group for R ′ ′′ is preferably in the range of 1 to 10.
- the carbon number of the cycloalkylene group for R ′ ′′ is preferably in the range of 3 to 10.
- the ring formed by bonding to each other may be substituted with a hydroxyl group, a group containing a carbonyl group (for example, an acyl group, an aldehyde group, alkoxycarbonyl, or the like), a cyano group, or the like.
- a group containing a carbonyl group for example, an acyl group, an aldehyde group, alkoxycarbonyl, or the like
- a cyano group or the like.
- the alkylene group for R ′ ′′ may have an ether bond in the alkylene chain.
- Examples of the solvent represented by the general formula (S2) include propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, diethylene glycol monomethyl.
- Ether acetate diethylene glycol monopropyl ether acetate, diethylene glycol monophenyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methyl-3-methoxy Propionate, ethyl-3-methoxypropionate, ethyl-3-ethoxypropionate, propyl-3-methoxypropionate, ethyl methoxyacetate, ethyl ethoxyacetate, 2-methoxybutylacetate, 3-methoxybutylacetate, 4 -Methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-ethyl-3-methoxybutyl acetate, 2-ethoxybutyl acetate, 4-ethoxybutyl acetate, 4-propoxy
- R ′′ and R ′′ ′′ are preferably unsubstituted alkyl groups
- R ′ ′′ is preferably an unsubstituted alkylene group
- R ′′ and R ′′ ′′ are methyl. It is more preferable that the group is either a group or an ethyl group, and it is even more preferable that R ′′ and R ′′ ′′ are methyl groups.
- the solvent represented by the general formula (S2) may be used in combination with one or more other organic solvents.
- the combined solvent in this case is not particularly limited as long as it can be mixed without being separated into the solvent represented by the general formula (S2), and the solvents represented by the general formula (S2) may be used in combination.
- the solvent represented by the general formula (S2) is mixed with a solvent selected from other ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents. Also good.
- One or more solvents can be used in combination, but it is preferable to use one solvent in order to obtain stable performance.
- the mixing ratio of the solvent represented by formula (S2) and the combination solvent is usually 20:80 to 99: 1, preferably 50:50 to 97: by mass. 3, more preferably 60:40 to 95: 5, and most preferably 60:40 to 90:10.
- the ether solvent containing one or more aromatic rings other than the ether solvent mentioned above can also be mentioned suitably.
- the solvent represented by the following general formula (S3) is preferable, and anisole is more preferable.
- R S represents an alkyl group.
- the alkyl group preferably has 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and still more preferably a methyl group.
- organic solvent contained in the developer an organic solvent used in an actinic ray-sensitive or radiation-sensitive composition described later can be used.
- the vapor pressure of the rinsing liquid (the vapor pressure as a whole in the case of a mixed solvent) is preferably 0.05 kPa or more and 5 kPa or less, more preferably 0.1 kPa or more and 5 kPa or less, and 0.12 kPa or more at 20 ° C. 3 kPa or less is more preferable.
- the vapor pressure of the rinse liquid By setting the vapor pressure of the rinse liquid to 0.05 kPa or more and 5 kPa or less, the temperature uniformity in the wafer surface is improved, and further, the swelling due to the penetration of the rinse solution is suppressed, and the dimensional uniformity in the wafer surface. Improves.
- organic solvents are used as the organic solvent contained in the rinsing liquid, and are selected from the group consisting of hydrocarbon solvents, ketone solvents, ester solvents, alcohol solvents, amide solvents, and ether solvents. It is preferable to use at least one organic solvent. Specific examples of these organic solvents are the same as those described for the developer.
- the organic solvent contained in the rinsing liquid in the case where EUV light (Extreme Ultra Violet) or EB (Electron Beam) is used in an exposure process described later, it is preferable to use a hydrocarbon solvent among the above organic solvents, It is more preferable to use an aliphatic hydrocarbon solvent.
- an aliphatic hydrocarbon solvent having 5 or more carbon atoms for example, pentane, hexane, octane, decane, undecane, dodecane, And an aliphatic hydrocarbon solvent having 8 or more carbon atoms, more preferably an aliphatic hydrocarbon solvent having 10 or more carbon atoms.
- the upper limit of the carbon number of the said aliphatic hydrocarbon solvent is not specifically limited, For example, 16 or less is mentioned, 14 or less is preferable and 12 or less is more preferable.
- decane, undecane, or dodecane is particularly preferable, and undecane is most preferable.
- An unsaturated hydrocarbon solvent can also be used as the hydrocarbon solvent contained in the rinse liquid, and examples thereof include unsaturated hydrocarbon solvents such as octene, nonene, decene, undecene, dodecene, and hexadecene.
- the number of double bonds or triple bonds that the unsaturated hydrocarbon solvent has is not particularly limited, and may be at any position of the hydrocarbon chain. Moreover, when an unsaturated hydrocarbon solvent has a double bond, cis body and trans body may be mixed.
- a hydrocarbon solvent especially an aliphatic hydrocarbon solvent
- the developer slightly soaked into the resist film after development is washed away, and swelling is further suppressed. Thus, the effect of suppressing pattern collapse is further exhibited.
- the organic solvent contained in the rinsing liquid a mixed solvent of the ester solvent and the hydrocarbon solvent or a mixed solvent of the ketone solvent and the hydrocarbon solvent may be used.
- the main component is a hydrocarbon solvent.
- the organic solvent contained in the rinse liquid is an embodiment in which at least one selected from the group consisting of the ester solvent and the ketone solvent is used from the viewpoint of being particularly effective for reducing residues after development. May be.
- the rinsing liquid contains at least one selected from the group consisting of ester solvents and ketone solvents, butyl acetate, isopentyl acetate (isoamyl acetate), n-pentyl acetate, ethyl 3-ethoxypropionate (EEP, Ethyl-3-ethoxypropionate) and at least one solvent selected from the group consisting of 2-heptanone as a main component, preferably at least selected from the group consisting of butyl acetate and 2-heptanone It is particularly preferable to contain one solvent as a main component.
- the rinsing liquid contains at least one selected from the group consisting of ester solvents and ketone solvents, it is selected from the group consisting of ester solvents, glycol ether solvents, ketone solvents, and alcohol solvents. It is preferable to contain as a subcomponent the propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monomethyl ether (PGME), ethyl acetate, ethyl lactate, methyl 3-methoxypropionate, cyclohexanone, methyl ethyl ketone, A solvent selected from the group consisting of ⁇ -butyrolactone, propanol, 3-methoxy-1-butanol, N-methylpyrrolidone, and propylene carbonate is preferred.
- PMEA propylene glycol monomethyl ether acetate
- PGME propylene glycol monomethyl ether
- ethyl acetate propylene glycol monomethyl ether
- an ester solvent when used as the organic solvent, it is preferable to use two or more ester solvents from the viewpoint that the above effects are further exhibited.
- an ester solvent preferably butyl acetate
- an ester solvent preferably propylene glycol monomethyl ether acetate (PGMEA)
- PMEA propylene glycol monomethyl ether acetate
- a glycol ether solvent may be used in addition to the ester solvent (one type or two or more types) from the viewpoint that the above effect is further exhibited.
- an ester solvent preferably butyl acetate
- a glycol ether solvent preferably propylene glycol monomethyl ether (PGME)
- PGME propylene glycol monomethyl ether
- ketone solvent preferably 2-heptanone
- ester solvent preferably propylene glycol monomethyl ether acetate (PGMEA)
- glycol ether solvent preferably, Propylene glycol monomethyl ether (PGME)
- main component means that the content of the organic solvent is 50 to 100% by mass, preferably 70 to 100% by mass, more preferably 80 to 100% by mass, More preferably, it is 90 to 100% by mass, particularly preferably 95 to 100% by mass.
- the content of the auxiliary component is preferably 0.1 to 20% by mass with respect to the total mass (100% by mass) of the main component, and preferably 0.5 to 10%. More preferably, it is more preferably 1 to 5% by weight.
- a plurality of organic solvents may be mixed, or may be used by mixing with an organic solvent other than the above.
- the solvent may be mixed with water, but the water content in the rinsing liquid is usually 60% by mass or less, preferably 30% by mass or less, more preferably 10% by mass or less, and most preferably 5% by mass or less. is there.
- a favorable rinse characteristic can be acquired by making a moisture content into 60 mass% or less.
- the treatment liquid of the present invention preferably contains a surfactant.
- a surfactant the same surfactants as those used in the actinic ray-sensitive or radiation-sensitive composition described later can be used.
- the content of the surfactant is usually 0.001 to 5% by mass, preferably 0.005 to 2% by mass, more preferably 0.01 to 0.5% by mass, based on the total mass of the treatment liquid. .
- the treatment liquid preferably contains an antioxidant. Thereby, generation
- amine-based antioxidants or phenol-based antioxidants are preferably used.
- amine antioxidants include 1-naphthylamine, phenyl-1-naphthylamine, p-octylphenyl-1-naphthylamine, p-nonylphenyl-1-naphthylamine, p-dodecylphenyl-1-naphthylamine, and phenyl- Naphthylamine antioxidants such as 2-naphthylamine; N, N′-diisopropyl-p-phenylenediamine, N, N′-diisobutyl-p-phenylenediamine, N, N′-diphenyl-p-phenylenediamine, N, N '-Di- ⁇ -naphthyl-p-phenylenediamine, N-phenyl
- phenolic antioxidants examples include 2,6-di-tert-butylphenol (hereinafter, tertiary butyl is abbreviated as t-butyl), 2,6-di-t-butyl-p-cresol, 2 , 6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,4-dimethyl-6-tert-butylphenol, 4,4′-methylenebis (2, 6-di-t-butylphenol), 4,4'-bis (2,6-di-t-butylphenol), 4,4'-bis (2-methyl-6-t-butylphenol), 2,2'- Methylenebis (4-methyl-6-t-butylphenol), 2,2′-methylenebis (4-ethyl-6-t-butylphenol), 4,4′-butylidenebis (3-methyl-6-t-butylphenol), 4 , 4 ' -Isopropylidenebis (2
- the content of the antioxidant is not particularly limited, but is preferably 0.0001 to 1% by mass, more preferably 0.0001 to 0.1% by mass, and more preferably 0.0001 to 0% with respect to the total mass of the treatment liquid. More preferred is 0.01 mass%.
- the content is 0.0001% by mass or more, an excellent antioxidant effect is obtained, and when the content is 1% by mass or less, residues after development and / or rinsing tend to be suppressed.
- the treatment liquid of the present invention preferably contains a basic compound.
- the basic compound include compounds exemplified as the basic compound (E) that can be contained in the actinic ray-sensitive or radiation-sensitive composition described later.
- the basic compounds that can be contained in the treatment liquid of the present invention the following nitrogen-containing compounds can be preferably used.
- the nitrogen-containing compound When the nitrogen-containing compound is contained in the developer, the nitrogen-containing compound interacts with a polar group generated in the resist film by the action of an acid, and can further improve the insolubility of the exposed portion with respect to the organic solvent.
- the interaction between the nitrogen-containing compound and the polar group means an action of forming a salt by reacting the nitrogen-containing compound and the polar group, an action of forming an ionic bond, and the like.
- the compound represented by Formula (1) is preferable.
- R 1 and R 2 each independently represent a hydrogen atom, a hydroxyl group, a formyl group, an alkoxy group, an alkoxycarbonyl group, a chain hydrocarbon group having 1 to 30 carbon atoms, or 3 to 3 carbon atoms.
- R 3 represents a hydrogen atom, a hydroxyl group, a formyl group, an alkoxy group, an alkoxycarbonyl group, an n-valent chain hydrocarbon group having 1 to 30 carbon atoms, an n-valent alicyclic hydrocarbon group having 3 to 30 carbon atoms, It is an n-valent aromatic hydrocarbon group having 6 to 14 carbon atoms, or an n-valent group formed by combining two or more of these groups.
- n is an integer of 1 or more. However, when n is 2 or more, the plurality of R 1 and R 2 may be the same or different. Further, any two of R 1 to R 3 may be bonded to form a ring structure together with the nitrogen atom to which each is bonded.
- Examples of the chain hydrocarbon group having 1 to 30 carbon atoms represented by R 1 and R 2 include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, and 2-methylpropyl. Group, 1-methylpropyl group, t-butyl group and the like.
- Examples of the alicyclic hydrocarbon group having 3 to 30 carbon atoms represented by R 1 and R 2 include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, and a norbornyl group.
- Examples of the aromatic hydrocarbon group having 6 to 14 carbon atoms represented by R 1 and R 2 include a phenyl group, a tolyl group, and a naphthyl group.
- Examples of the group formed by combining two or more of these groups represented by R 1 and R 2 include aralkyl groups having 6 to 12 carbon atoms such as benzyl, phenethyl, naphthylmethyl, and naphthylethyl groups. Is mentioned.
- Examples of the n-valent chain hydrocarbon group having 1 to 30 carbon atoms represented by R 3 include groups exemplified as the chain hydrocarbon group having 1 to 30 carbon atoms represented by R 1 and R 2 above. And a group obtained by removing (n-1) hydrogen atoms from the same group.
- Examples of the alicyclic hydrocarbon group having 3 to 30 carbon atoms represented by R 3 include the same groups as those exemplified as the cyclic hydrocarbon group having 3 to 30 carbon atoms represented by R 1 and R 2. And a group obtained by removing (n-1) hydrogen atoms from the group.
- Examples of the aromatic hydrocarbon group having 6 to 14 carbon atoms represented by R 3 are the same as those exemplified as the aromatic hydrocarbon group having 6 to 14 carbon atoms represented by R 1 and R 2 . And a group obtained by removing (n-1) hydrogen atoms from the group.
- the group formed by combining two or more of these groups represented by R 3 is the same as the group exemplified as a group formed by combining two or more of these groups represented by R 1 and R 2 . And a group obtained by removing (n-1) hydrogen atoms from the group.
- the groups represented by R 1 to R 3 may be substituted.
- the substituent include a methyl group, an ethyl group, a provir group, an n-butyl group, a t-butyl group, a hydroxyl group, a carboxy group, a halogen atom, and an alkoxy group.
- the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
- alkoxy group include a methoxy group, an ethoxy group, a propoxy group, and a butoxy group.
- Examples of the compound represented by the above formula (1) include (cyclo) alkylamine compounds, nitrogen-containing heterocyclic compounds, amide group-containing compounds, and urea compounds.
- Examples of (cyclo) alkylamine compounds include compounds having one nitrogen atom, compounds having two nitrogen atoms, and compounds having three or more nitrogen atoms.
- Examples of (cyclo) alkylamine compounds having one nitrogen atom include mono (cyclo) alkylamines such as n-hexylamine, n-heptylamine, n-octylamine, n-nonylamine, 1-aminodecane, and cyclohexylamine.
- Di (cyclo) alkylamines such as amine and dicyclohexylamine; triethylamine, tri-n-propylamine, tri-n-butylamine, tri-n-pentylamine, tri-n-hexylamine, tri-n-heptylamine , Tri-n-octylamine, tri-n-nonylami , Tri-n-decylamine, cyclohexyldimethylamine, methyldicyclohexylamine, and tri (cyclo) alkylamines such as tricyclohexylamine; substituted alkylamines such as triethanolamine; aniline, N-
- Examples of the (cyclo) alkylamine compound having two nitrogen atoms include ethylenediamine, tetramethylethylenediamine, tetramethylenediamine, hexamethylenediamine, 4,4′-diaminodiphenylmethane, 4,4′-diaminodiphenyl ether, and 4,4 ′.
- Examples of the (cyclo) alkylamine compound having 3 or more nitrogen atoms include polymers such as polyethyleneimine, polyallylamine, and 2-dimethylaminoethylacrylamide.
- nitrogen-containing heterocyclic compounds include nitrogen-containing aromatic heterocyclic compounds and nitrogen-containing aliphatic heterocyclic compounds.
- nitrogen-containing aromatic heterocyclic compound examples include imidazole, 4-methylimidazole, 4-methyl-2-phenylimidazole, benzimidazole, 2-phenylbenzimidazole, 1-benzyl-2-methylimidazole, and 1-benzyl- Imidazoles such as 2-methyl-1H-imidazole; pyridine, 2-methylpyridine, 4-methylpyridine, 2-ethylpyridine, 4-ethylpyridine, 2-phenylpyridine, 4-phenylpyridine, 2-methyl-4- And pyridines such as phenylpyridine, nicotine, nicotinic acid, nicotinamide, quinoline, 4-hydroxyquinoline, 8-oxyquinoline, acridine, and 2,2 ′: 6 ′, 2 ′′ -terpyridine.
- nitrogen-containing aliphatic heterocyclic compound examples include piperazine such as piperazine and 1- (2-hydroxyethyl) piperazine; pyrazine, pyrazole, pyridazine, quinosaline, purine, pyrrolidine, proline, piperidine, piperidine ethanol, 3-piperidino -1,2-propanediol, morpholine, 4-methylmorpholine, 1- (4-morpholinyl) ethanol, 4-acetylmorpholine, 3- (N-morpholino) -1,2-propanediol, 1,4-dimethylpiperazine , And 1,4-diazabicyclo [2.2.2] octane.
- piperazine such as piperazine and 1- (2-hydroxyethyl) piperazine
- pyrazine pyrazole, pyridazine, quinosaline
- purine pyrrolidine, proline
- piperidine piperidine ethanol
- Examples of the amide group-containing compound include Nt-butoxycarbonyldi-n-octylamine, Nt-butoxycarbonyldi-n-nonylamine, Nt-butoxycarbonyldi-n-decylamine, and Nt-butoxy.
- urea compounds include urea, methylurea, 1,1-dimethylurea, 1,3-dimethylurea, 1,1,3,3-tetramethylurea, and 1,3-diphenylurea.
- nitrogen-containing compounds having an SP value of 18 or less are preferably used from the viewpoint of suppressing development defects. This is because a nitrogen-containing compound having an SP value of 18 or less has good affinity with a rinsing liquid used in a rinsing process described later, and can suppress development defects such as precipitation.
- a (cyclo) alkylamine compound or a nitrogen-containing aliphatic heterocyclic compound that satisfies the above-described conditions is preferable.
- 1-aminodecane, di-n-octylamine, tri-n-octylamine Or tetramethylethylenediamine is more preferred.
- the following table shows the SP values and the like of these nitrogen-containing aliphatic heterocyclic compounds.
- the content of the basic compound (preferably a nitrogen-containing compound) in the treatment liquid is not particularly limited, but is preferably 10% by mass or less based on the total amount of the treatment liquid in terms of more excellent effects of the present invention. 5 to 5% by mass is preferable. In the present invention, only one kind of the above nitrogen-containing compounds may be used, or two or more kinds having different chemical structures may be used in combination.
- non-chemical amplification resists examples include the following.
- Resist materials whose solubility changes when the main chain is cleaved by irradiation with g-line, h-line, i-line, KrF, ArF, EB, EUV or the like, and the molecular weight is lowered (for example, JP 2013-210411 A)
- the main component is a copolymer of an ⁇ -chloroacrylic acid ester compound and an ⁇ -methylstyrene compound described in paragraphs 0025 to 0029 and 0056 of the publication and paragraphs 0032 to 0036 and 0063 of US Patent Publication 2015/0008211.
- Resist materials etc. (2) Resist materials such as hydrogen silsesquioxane (HSQ) accompanied by silanol condensation reaction caused by g-line, h-line, i-line, KrF, ArF, EB or EUV, chlorine-substituted calixarene, etc.
- HQ hydrogen silsesquioxane
- g Metal complexes that absorb light such as wire, h-line, i-line, KrF, ArF, EB or EUV (magnesium, chromium, manganese, iron, cobalt, nickel, copper, zinc, silver, cadmium, indium, tin , Antimony, cesium, zirconium, hafnium and the like, and titanium, zirconium, hafnium are preferable from the viewpoint of pattern formation), and are used in combination with a ligand elimination and / or photoacid generator.
- Resist with replacement process paragraphs 0017 to 0033, 0037 to 0047 of JP2015-075500, JP2012 185485 JP paragraphs 0017 ⁇ 0032,0043 ⁇ 0044, the resist material described in U.S. paragraphs 0042 - 0051,0066 such patent publications 2012/0208125) and the like.
- the above-described processing liquid can be suitably applied to a silicon-based resist for the purpose of solving the same problems as in the present application.
- the silicon resist include resist materials described in paragraphs 0010 to 0062 and paragraphs 0129 to 0165 described in JP-A-2008-83384.
- the pattern forming method of the present invention includes a resist film forming step of forming a resist film using an actinic ray-sensitive or radiation-sensitive composition (hereinafter also referred to as “resist composition”), and an exposure step of exposing the resist film. And a processing step of processing the exposed resist film with the processing liquid described above. According to the pattern forming method of the present invention, since the above-described processing liquid is used, the occurrence of pattern collapse in the resist L / S pattern and the occurrence of defective omission in the resist C / H pattern can be suppressed at the same time.
- resist composition actinic ray-sensitive or radiation-sensitive composition
- the resist film forming step is a step of forming a resist film using an actinic ray-sensitive or radiation-sensitive composition, and can be performed, for example, by the following method.
- a resist film actinic ray-sensitive or radiation-sensitive composition film
- each component described later is dissolved in a solvent and activated.
- a light-sensitive or radiation-sensitive composition is prepared, filtered as necessary, and then applied onto a substrate.
- the filter is preferably made of polytetrafluoroethylene, polyethylene, or nylon having a pore size of 0.1 microns or less, more preferably 0.05 microns or less, and still more preferably 0.03 microns or less.
- the actinic ray-sensitive or radiation-sensitive composition is applied to a substrate (eg, silicon or silicon dioxide coating) used for manufacturing an integrated circuit element by an appropriate application method such as a spinner. Thereafter, it is dried to form a resist film. If necessary, various base films (inorganic films, organic films, or antireflection films) may be formed below the resist film.
- a substrate eg, silicon or silicon dioxide coating
- an appropriate application method such as a spinner.
- Heating can be performed by means provided in a normal exposure developing machine, and may be performed using a hot plate or the like.
- the heating temperature is preferably 80 to 180 ° C., more preferably 80 to 150 ° C., further preferably 80 to 140 ° C., and particularly preferably 80 to 130 ° C.
- the heating time is preferably 30 to 1000 seconds, more preferably 60 to 800 seconds, and still more preferably 60 to 600 seconds.
- the film thickness of the resist film is generally 200 nm or less, preferably 100 nm or less.
- the thickness of the resist film to be formed is preferably 50 nm or less. If the film thickness is 50 nm or less, pattern collapse is less likely to occur when a development process described later is applied, and better resolution performance is obtained. More preferably, the film thickness ranges from 15 nm to 45 nm. If the film thickness is 15 nm or more, sufficient etching resistance can be obtained. More preferably, the film thickness ranges from 15 nm to 40 nm. When the film thickness is in this range, etching resistance and better resolution performance can be satisfied at the same time.
- an upper layer film may be formed on the upper layer of the resist film.
- the upper layer film can be formed using, for example, an upper layer film forming composition containing a hydrophobic resin, an acid generator, and a basic compound.
- the upper layer film and the composition for forming the upper layer film are as described below.
- An exposure process is a process of exposing the said resist film, for example, can be performed with the following method.
- the resist film formed as described above is irradiated with actinic rays or radiation through a predetermined mask. Note that in electron beam irradiation, drawing (direct drawing) without using a mask is common.
- a pre-exposure bake step also referred to as a post-application bake step (PB; Prebake)
- PB post-application bake step
- actinic light or a radiation examples include KrF excimer laser, ArF excimer laser, EUV light (Extreme Ultra Violet), an electron beam (EB, Electron Beam), etc.
- the exposure may be immersion exposure.
- a post-exposure bake step PEB; Post Exposure Bake
- the post-exposure baking process accelerates the reaction of the exposed area, and the sensitivity or pattern shape becomes better.
- the heating temperature is preferably 80 to 150 ° C, more preferably 80 to 140 ° C, and still more preferably 80 to 130 ° C.
- the heating time is preferably 30 to 1000 seconds, more preferably 60 to 800 seconds, and still more preferably 60 to 600 seconds. Heating can be performed by means provided in a normal exposure / developing machine, and may be performed using a hot plate or the like.
- the heating temperature and heating time in the pre-exposure baking process are the same as the heating temperature and heating time in the post-exposure baking process.
- the development step is a step of developing the exposed resist film with a developer.
- a development method for example, a method in which a substrate is immersed in a tank filled with a developer for a certain period of time (dip method), a method in which the developer is raised on the surface of the substrate by surface tension and is left stationary for a certain time (paddle) Method), a method of spraying a developer on the substrate surface (spray method), and a method of continuously discharging the developer while scanning the developer discharge nozzle at a constant speed on a substrate rotating at a constant speed (dynamic dispensing). Law) etc.
- dip method a method in which a substrate is immersed in a tank filled with a developer for a certain period of time
- paddle a method in which the developer is raised on the surface of the substrate by surface tension and is left stationary for a certain time
- spray method a method of spraying a developer on the substrate surface
- dynamic dispensing a method of continuously discharging the developer while scanning the developer discharge nozzle at a constant speed on a substrate rotating at a constant speed
- the development time is not particularly limited as long as the resin in the unexposed area is sufficiently dissolved, and is usually 10 to 300 seconds, preferably 20 to 120 seconds.
- the temperature of the developer is preferably 0 to 50 ° C, more preferably 15 to 35 ° C.
- the developer used in the developing step it is preferable to use the above-described processing solution.
- the developer is as described above.
- development with an alkaline developer may be performed (so-called double development).
- the rinsing step is a step of rinsing (rinsing) with a rinsing liquid after the developing step.
- the developed wafer is cleaned using the rinsing liquid.
- the method of the cleaning process is not particularly limited. For example, a method of continuing to discharge the rinse liquid onto the substrate rotating at a constant speed (rotary discharge method), and immersing the substrate in a tank filled with the rinse liquid for a certain period of time.
- a method (dip method) and a method (spray method) of spraying a rinsing liquid onto the substrate surface can be applied.
- a cleaning process is performed by a rotary discharge method, and the substrate is rotated at 2000 rpm to 4000 rpm after cleaning. It is preferable to remove the rinse liquid from the substrate by rotating the film by a number.
- the rinsing time is not particularly limited, but is usually 10 to 300 seconds.
- the time is preferably 10 seconds to 180 seconds, and most preferably 20 seconds to 120 seconds.
- the temperature of the rinse liquid is preferably 0 to 50 ° C., more preferably 15 to 35 ° C.
- a process of removing the developing solution or the rinsing liquid adhering to the pattern with a supercritical fluid can be performed.
- a heat treatment can be performed in order to remove the solvent remaining in the pattern.
- the heating temperature is not particularly limited as long as a good resist pattern can be obtained, and is usually 40 to 160 ° C.
- the heating temperature is preferably 50 to 150 ° C, and most preferably 50 to 110 ° C.
- the heating time is not particularly limited as long as a good resist pattern can be obtained, but it is usually 15 to 300 seconds, and preferably 15 to 180 seconds.
- the rinse liquid it is preferable to use the above-described treatment liquid.
- the explanation of the rinse liquid is as described above.
- At least one of the developer and the rinsing liquid is the above-described processing liquid, and it is particularly preferable that the rinsing liquid is the above-described processing liquid.
- the developer and the rinse liquid are stored in a waste liquid tank through a pipe after use.
- a waste liquid tank for example, if an ester solvent is used as the developer and a hydrocarbon solvent is used as the rinse liquid, the resist dissolved in the developer is deposited, and adheres to the wafer side rear surface, the piping side surface, and the like. Dirty equipment.
- a solvent in which the resist is dissolved is again passed through the pipe.
- a method of passing through the piping after cleaning with the rinsing liquid, cleaning the back and side surfaces of the substrate with a solvent that dissolves the resist, or allowing the solvent that the resist solvent does not contact with the resist to pass through the piping.
- the solvent passed through the pipe is not particularly limited as long as it can dissolve the resist, and examples thereof include the solvent used as the developer described above.
- PGMEA propylene glycol monomethyl ether acetate
- propylene glycol monoethyl ether acetate propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol monomethyl ether propionate, propylene glycol monoethyl ether propionate
- Ethylene glycol monomethyl ether acetate ethylene glycol monoethyl ether acetate
- PGME propylene glycol monomethyl ether
- propylene glycol monoethyl ether propylene glycol monopropyl ether
- propylene glycol monobutyl ether ethylene glycol monomethyl ether, ethylene glycol mono Chirueteru, 2-heptanone, ethyl lactate, 1-propanol
- actinic ray or radiation sensitive composition resist composition
- the actinic ray-sensitive or radiation-sensitive composition that is preferably used in combination with the treatment liquid of the present invention will be described in detail.
- components that can be contained in the actinic ray-sensitive or radiation-sensitive composition will be described first.
- Resin (A) Resin
- the actinic ray-sensitive or radiation-sensitive composition preferably used in combination with the treatment liquid of the present invention preferably contains “resin (A))”.
- Resin (A) is at least (i) a repeating unit having a group that decomposes by the action of an acid to generate a carboxyl group (may further have a repeating unit having a phenolic hydroxyl group), or at least (ii) It has a repeating unit having a phenolic hydroxyl group.
- Examples of the repeating unit having a phenolic hydroxyl group contained in the resin (A) include a repeating unit represented by the following general formula (I).
- R 41 , R 42 and R 43 each independently represents a hydrogen atom, an alkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group.
- R 42 may form a ring with Ar 4, R 42 in this case represents a single bond or an alkylene group.
- X 4 represents a single bond, —COO—, or —CONR 64 —, and R 64 represents a hydrogen atom or an alkyl group.
- L 4 represents a single bond or an alkylene group.
- Ar 4 represents an (n + 1) -valent aromatic ring group, and when bonded to R 42 to form a ring, represents an (n + 2) -valent aromatic ring group.
- n represents an integer of 1 to 5.
- the alkyl group of R 41 , R 42 and R 43 in the general formula (I) is preferably a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec which may have a substituent.
- -An alkyl group having 20 or less carbon atoms such as a butyl group, a hexyl group, a 2-ethylhexyl group, an octyl group, or a dodecyl group, preferably an alkyl group having 8 or less carbon atoms, more preferably 3 or less carbon atoms It is an alkyl group.
- the cycloalkyl group represented by R 41 , R 42 and R 43 in the general formula (I) may be monocyclic or polycyclic. Of these, a monocyclic cycloalkyl group having 3 to 8 carbon atoms such as a cyclopropyl group, a cyclopentyl group and a cyclohexyl group which may have a substituent is preferable.
- Examples of the halogen atom of R 41 , R 42 and R 43 in the general formula (I) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferred.
- the alkyl group contained in the alkoxycarbonyl group of R 41 , R 42 , and R 43 in the general formula (I) the same alkyl groups as those described above for R 41 , R 42 , and R 43 are preferable.
- Preferred substituents in each of the above groups include, for example, alkyl groups, cycloalkyl groups, aryl groups, amino groups, amide groups, ureido groups, urethane groups, hydroxyl groups, carboxyl groups, halogen atoms, alkoxy groups, thioether groups, acyls. Groups, acyloxy groups, alkoxycarbonyl groups, cyano groups, nitro groups and the like, and the substituent preferably has 8 or less carbon atoms.
- Ar 4 represents an (n + 1) -valent aromatic ring group.
- n + 1) -valent aromatic ring group in the case where n is an integer of 2 or more include (n-1) arbitrary hydrogen atoms removed from the above-described specific examples of the divalent aromatic ring group.
- the group formed can be preferably mentioned.
- the (n + 1) -valent aromatic ring group may further have a substituent.
- Examples of the substituent that the above-described alkyl group, cycloalkyl group, alkoxycarbonyl group, alkylene group, and (n + 1) -valent aromatic ring group may have include R 41 , R 42 , and R 43 in formula (I).
- Alkoxy groups such as alkyl groups, methoxy groups, ethoxy groups, hydroxyethoxy groups, propoxy groups, hydroxypropoxy groups, and butoxy groups mentioned in the above; aryl groups such as phenyl groups; and the like.
- R 64 is a hydrogen atom, or an alkyl a group
- R 64 is a hydrogen atom, or an alkyl a group
- R 64 is a hydrogen atom, or an alkyl a group
- R 64 is a hydrogen atom, or an alkyl a group
- R 64 in which may have a substituent methyl group, an ethyl group, a propyl group
- An alkyl group having 20 or less carbon atoms such as isopropyl group, n-butyl group, sec-butyl group, hexyl group, 2-ethylhexyl group, octyl group, and dodecyl group is preferable, and an alkyl group having 8 or less carbon atoms is more preferable.
- X 4 is preferably a single bond, —COO— or —CONH—, and more preferably a single bond or —COO—.
- the alkylene group for L 4 is preferably an alkylene group having 1 to 8 carbon atoms, such as an optionally substituted methylene group, ethylene group, propylene group, butylene group, hexylene group, and octylene group.
- Ar 4 an optionally substituted aromatic ring group having 6 to 18 carbon atoms is more preferable, and a benzene ring group, a naphthalene ring group, or a biphenylene ring group is particularly preferable.
- the repeating unit represented by the general formula (I) preferably has a hydroxystyrene structure. That is, Ar 4 is preferably a benzene ring group.
- Preferred examples of the repeating unit having a phenolic hydroxyl group that the resin (A) has include a repeating unit represented by the following general formula (p1).
- R in the general formula (p1) represents a hydrogen atom, a halogen atom, or a linear or branched alkyl group having 1 to 4 carbon atoms. A plurality of R may be the same or different. R in the general formula (p1) is preferably a hydrogen atom.
- Ar in the general formula (p1) represents an aromatic ring.
- the aromatic ring may have a substituent having 6 to 18 carbon atoms such as a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, and a phenanthrene ring.
- Hydrocarbon rings and heterocycles such as, for example, thiophene rings, furan rings, pyrrole rings, benzothiophene rings, benzofuran rings, benzopyrrole rings, triazine rings, imidazole rings, benzimidazole rings, triazole rings, thiadiazole rings, and thiazole rings
- An aromatic heterocyclic ring containing a ring can be mentioned. Of these, a benzene ring is preferred.
- M in the general formula (p1) represents an integer of 1 to 5, preferably 1.
- the content of the repeating unit having a phenolic hydroxyl group is preferably from 0 to 50 mol%, more preferably from 0 to 45 mol%, still more preferably from 0 to 40 mol%, based on all repeating units in the resin (A). is there.
- the repeating unit having a group that decomposes by the action of an acid and generates a carboxyl group in the resin (A) is a repeating unit having a group in which a hydrogen atom of the carboxyl group is substituted with a group that decomposes and leaves by the action of an acid It is.
- R 36 to R 39 each independently represents an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or an alkenyl group.
- R 36 and R 37 may be bonded to each other to form a ring.
- R 01 and R 02 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or an alkenyl group.
- the resin (A) is preferably a repeating unit represented by the following general formula (AI).
- Xa 1 represents a hydrogen atom or an alkyl group which may have a substituent.
- T represents a single bond or a divalent linking group.
- Rx 1 to Rx 3 each independently represents an alkyl group (straight or branched) or a cycloalkyl group (monocyclic or polycyclic). However, when all of Rx 1 to Rx 3 are alkyl groups (linear or branched), at least two of Rx 1 to Rx 3 are preferably methyl groups. Two of Rx 1 to Rx 3 may combine to form a cycloalkyl group (monocyclic or polycyclic).
- Examples of the optionally substituted alkyl group represented by Xa 1 include a methyl group or a group represented by —CH 2 —R 11 .
- R 11 represents a halogen atom (such as a fluorine atom), a hydroxyl group or a monovalent organic group, and examples thereof include an alkyl group having 5 or less carbon atoms and an acyl group having 5 or less carbon atoms, preferably 3 carbon atoms.
- the following alkyl groups are preferable, and a methyl group is more preferable.
- Xa 1 is preferably a hydrogen atom, a methyl group, a trifluoromethyl group, a hydroxymethyl group, or the like.
- Examples of the divalent linking group for T include an alkylene group, —COO—Rt— group, and —O—Rt— group.
- Rt represents an alkylene group or a cycloalkylene group.
- T is preferably a single bond or a —COO—Rt— group.
- Rt is preferably an alkylene group having 1 to 5 carbon atoms, more preferably a —CH 2 — group, a — (CH 2 ) 2 — group, or a — (CH 2 ) 3 — group.
- the alkyl group of Rx 1 to Rx 3 is preferably an alkyl group having 1 to 4 carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, and t-butyl group.
- Examples of the cycloalkyl group of Rx 1 to Rx 3 include a monocyclic cycloalkyl group such as a cyclopentyl group and a cyclohexyl group, a polycyclic group such as a norbornyl group, a tetracyclodecanyl group, a tetracyclododecanyl group, and an adamantyl group.
- a cycloalkyl group is preferred.
- Examples of the cycloalkyl group formed by combining two of Rx 1 to Rx 3 include a cyclopentyl group and a monocyclic cycloalkyl group such as a cyclohexyl group, a norbornyl group, a tetracyclodecanyl group, a tetracyclododecanyl group, And a polycyclic cycloalkyl group such as an adamantyl group is preferred.
- a monocyclic cycloalkyl group having 5 to 6 carbon atoms is more preferable.
- the cycloalkyl group formed by combining two of Rx 1 to Rx 3 is, for example, a group in which one of the methylene groups constituting the ring has a heteroatom such as an oxygen atom or a heteroatom such as a carbonyl group. It may be replaced.
- the repeating unit represented by the general formula (AI) preferably has, for example, an embodiment in which Rx 1 is a methyl group or an ethyl group, and Rx 2 and Rx 3 are bonded to form the above-described cycloalkyl group.
- Each of the above groups may have a substituent.
- substituents include an alkyl group (1 to 4 carbon atoms), a halogen atom, a hydroxyl group, an alkoxy group (1 to 4 carbon atoms), a carboxyl group, and Examples thereof include alkoxycarbonyl groups (having 2 to 6 carbon atoms), and those having 8 or less carbon atoms are preferred.
- the repeating unit represented by formula (AI) is preferably an acid-decomposable (meth) acrylic acid tertiary alkyl ester-based repeating unit (Xa 1 represents a hydrogen atom or a methyl group, and T is a single bond. Is a repeating unit).
- Xa 1 represents a hydrogen atom or a methyl group
- T is a single bond.
- Rx 1 ⁇ Rx 3 each a repeating unit represents a linear or branched alkyl group, more preferably, that each independently is Rx 1 ⁇ Rx 3, represents a linear alkyl group Unit.
- (meth) acrylic acid means acrylic acid and / or methacrylic acid. The same applies to (meth) acrylic groups and (meth) acrylates.
- Rx and Xa 1 represent a hydrogen atom, CH 3 , CF 3 , or CH 2 OH.
- Rxa and Rxb each represents an alkyl group having 1 to 4 carbon atoms.
- Z represents a substituent containing a polar group, and when there are a plurality of them, each is independent.
- p represents 0 or a positive integer.
- Examples of the substituent containing a polar group represented by Z include a linear, branched or cyclic alkyl group having a hydroxyl group, a cyano group, an amino group, an alkylamide group or a sulfonamide group, preferably a hydroxyl group It is an alkyl group having As the branched alkyl group, an isopropyl group is particularly preferable.
- the content of the repeating unit having a group capable of decomposing by the action of an acid to generate a carboxyl group is preferably from 15 to 90 mol%, more preferably from 20 to 90 mol%, based on all repeating units in the resin (A). It is more preferably 25 to 80 mol%, particularly preferably 30 to 70 mol%.
- the resin (A) preferably further contains a repeating unit having a lactone group.
- the lactone group may be any group as long as it contains a lactone structure, but is preferably a group containing a 5- to 7-membered ring lactone structure, and forms a bicyclo structure or a spiro structure in the 5- to 7-membered ring lactone structure. More preferred are those in which other ring structures are condensed.
- the repeating unit having a lactone group preferably has a repeating unit containing a group having a lactone structure represented by any of the following general formulas (LC1-1) to (LC1-16).
- a preferable lactone structure is a group represented by the general formula (LC1-1), (LC1-4), (LC1-5), (LC1-6), (LC1-13), or (LC1-14). . Further, a group having a lactone structure may be directly bonded to the main chain.
- the lactone structure portion may or may not have a substituent (Rb 2 ).
- Preferred substituents (Rb 2 ) include an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 4 to 7 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, and a carboxyl group.
- n2 represents an integer of 0 to 4. When n2 is 2 or more, a plurality of Rb 2 may be the same or different, and a plurality of Rb 2 may be bonded to form a ring.
- Examples of the repeating unit containing a group having a lactone structure represented by any of the general formulas (LC1-1) to (LC1-16) include a repeating unit represented by the following general formula (AI) be able to.
- Rb 0 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms.
- substituents that the alkyl group represented by Rb 0 may have include a hydroxyl group and a halogen atom.
- the halogen atom for Rb 0 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- Rb 0 is preferably a hydrogen atom or a methyl group.
- Ab is a single bond, an alkylene group, a divalent linking group having a monocyclic or polycyclic alicyclic hydrocarbon structure, an ether group, an ester group, a carbonyl group, a carboxyl group, or a divalent group obtained by combining these. To express. Preferably, it is a single bond or a linking group represented by —Ab 1 —CO 2 —.
- Ab 1 is a linear or branched alkylene group or a monocyclic or polycyclic cycloalkylene group, preferably a methylene group, an ethylene group, a cyclohexylene group, an adamantylene group, or a norbornylene group.
- V represents a group represented by any one of the general formulas (LC1-1) to (LC1-16).
- the repeating unit having a group containing a lactone structure usually has an optical isomer, but any optical isomer may be used.
- One optical isomer may be used alone, or a plurality of optical isomers may be mixed and used.
- the optical purity (ee) thereof is preferably 90 or more, more preferably 95 or more.
- repeating unit having a group containing a lactone structure examples include:
- the content of the repeating unit having a lactone group is preferably from 1 to 65 mol%, more preferably from 1 to 30 mol%, still more preferably from 5 to 25 mol%, based on all repeating units in the resin (A). ⁇ 20 mol% is particularly preferred.
- the resin (A) can further have a repeating unit containing an organic group having a polar group, particularly a repeating unit having an alicyclic hydrocarbon structure substituted with a polar group. This improves the substrate adhesion and / or developer affinity.
- the alicyclic hydrocarbon structure of the alicyclic hydrocarbon structure substituted with a polar group is preferably an adamantyl group, a diamantyl group, or a norbornane group.
- the polar group is preferably a hydroxyl group or a cyano group. Specific examples of the repeating unit having a polar group are listed below, but the present invention is not limited thereto.
- the content thereof is preferably 1 to 50 mol% with respect to all repeating units in the resin (A), and preferably 1 to 30 mol. % Is more preferable, 5 to 25 mol% is further preferable, and 5 to 20 mol% is particularly preferable.
- a repeating unit having a group capable of generating an acid (photoacid generating group) upon irradiation with actinic rays or radiation can also be included.
- the repeating unit having this photoacid-generating group corresponds to the compound (B) that generates an acid upon irradiation with actinic rays or radiation described later.
- Examples of such a repeating unit include a repeating unit represented by the following general formula (4).
- R 41 represents a hydrogen atom or a methyl group.
- L 41 represents a single bond or a divalent linking group.
- L 42 represents a divalent linking group.
- W represents a structural site that decomposes upon irradiation with actinic rays or radiation to generate an acid in the side chain.
- examples of the repeating unit represented by the general formula (4) include repeating units described in paragraphs [0094] to [0105] of JP-A No. 2014-041327.
- the content of the repeating unit having a photoacid-generating group is preferably 1 to 40 mol% with respect to all the repeating units in the resin (A). More preferably, it is 5 to 35 mol%, and still more preferably 5 to 30 mol%.
- Resin (A) can be synthesized according to a conventional method (for example, radical polymerization).
- general synthesis methods include a batch polymerization method in which a monomer species and an initiator are dissolved in a solvent and polymerization is performed by heating, and a solution of the monomer species and the initiator in the heating solvent over 1 to 10 hours.
- Examples include a dropping polymerization method that is added dropwise, and a dropping polymerization method is preferred.
- reaction solvent examples include ethers such as tetrahydrofuran, 1,4-dioxane, and diisopropyl ether; ketones such as methyl ethyl ketone and methyl isobutyl ketone; ester solvents such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide Solvent; Solvent that dissolves actinic ray-sensitive or radiation-sensitive compositions such as propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and cyclohexanone described below. More preferably, the polymerization is performed using the same solvent as that used in the actinic ray-sensitive or radiation-sensitive composition. Thereby, generation
- the polymerization reaction is preferably carried out in an inert gas atmosphere such as nitrogen and argon.
- Polymerization is initiated using a commercially available radical initiator (such as an azo initiator and peroxide) as the polymerization initiator.
- a commercially available radical initiator such as an azo initiator and peroxide
- an azo initiator is preferable, and an azo initiator having an ester group, a cyano group, or a carboxyl group is preferable.
- Preferred initiators include azobisisobutyronitrile, azobisdimethylvaleronitrile, dimethyl 2,2′-azobis (2-methylpropionate), and the like.
- an initiator is added or added in portions, and after completion of the reaction, it is put into a solvent and a desired polymer is recovered by a method such as powder or solid recovery.
- the concentration of the reaction is 5 to 50% by mass, preferably 10 to 30% by mass.
- the reaction temperature is usually 10 ° C. to 150 ° C., preferably 30 ° C. to 120 ° C., more preferably 60 to 100 ° C.
- Purification is a liquid-liquid extraction method that removes residual monomers and oligomer components by washing with water or an appropriate solvent, a purification method in a solution state such as ultrafiltration that extracts and removes only those having a specific molecular weight or less, In a solid state such as a reprecipitation method for removing residual monomers by coagulating the resin in the poor solvent by dropping the resin solution into the poor solvent, and washing the filtered resin slurry with the poor solvent Ordinary methods such as the purification method can be applied.
- the weight average molecular weight of the resin (A) is preferably from 1,000 to 200,000, more preferably from 3,000 to 20,000, still more preferably from 5,000 to 15, in terms of polystyrene by GPC method. 000.
- the weight average molecular weight is preferably from 1,000 to 200,000, more preferably from 3,000 to 20,000, still more preferably from 5,000 to 15, in terms of polystyrene by GPC method. 000.
- Another particularly preferable form of the weight average molecular weight of the resin (A) is 3,000 to 9,500 in terms of polystyrene by GPC method.
- the degree of dispersion is usually 1 to 5, preferably 1 to 3, more preferably 1.2 to 3.0, and particularly preferably 1.2 to 2.0. .
- the smaller the degree of dispersion the better the resolution and resist shape, the smoother the sidewall of the resist pattern, and the better the roughness.
- the content of the resin (A) is preferably 50 to 99.9% by mass and more preferably 60 to 99.0% by mass based on the total solid content.
- the resin (A) may be used alone or in combination.
- the resin (A) may contain a repeating unit represented by the following general formula (VI).
- R 61 , R 62 and R 63 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group.
- R 62 may be bonded to Ar 6 to form a ring, and R 62 in this case represents a single bond or an alkylene group.
- X 6 represents a single bond, —COO—, or —CONR 64 —.
- R 64 represents a hydrogen atom or an alkyl group.
- L 6 represents a single bond or an alkylene group.
- Ar 6 represents an (n + 1) -valent aromatic ring group, and represents an (n + 2) -valent aromatic ring group when bonded to R 62 to form a ring.
- Y 2 independently represents a hydrogen atom or a group capable of leaving by the action of an acid when n ⁇ 2. However, at least one of Y 2 represents a group capable of leaving by the action of an acid.
- n represents an integer of 1 to 4.
- a structure represented by the following general formula (VI-A) is more preferable.
- L 1 and L 2 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a group in which an alkylene group and an aryl group are combined.
- M represents a single bond or a divalent linking group.
- Q represents an alkyl group, a cycloalkyl group which may contain a hetero atom, an aryl group which may contain a hetero atom, an amino group, an ammonium group, a mercapto group, a cyano group or an aldehyde group. At least two of Q, M, and L 1 may combine to form a ring (preferably a 5-membered or 6-membered ring).
- the repeating unit represented by the general formula (VI) is preferably a repeating unit represented by the following general formula (3).
- Ar 3 represents an aromatic ring group.
- R 3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyl group, or a heterocyclic group.
- M 3 represents a single bond or a divalent linking group.
- Q 3 represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group. At least two of Q 3 , M 3 and R 3 may be bonded to form a ring.
- the aromatic ring group represented by Ar 3 is the same as Ar 6 in the general formula (VI) when n in the general formula (VI) is 1, preferably a phenylene group or a naphthylene group, and more A phenylene group is preferred.
- repeating unit represented by the general formula (VI) are shown below, but the present invention is not limited thereto.
- Resin (A) preferably contains a repeating unit represented by the following general formula (4).
- R 41 , R 42 and R 43 each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkoxycarbonyl group.
- R 42 may be bonded to L 4 to form a ring, and R 42 in this case represents an alkylene group.
- L 4 represents a single bond or a divalent linking group, and in the case of forming a ring with R 42 , represents a trivalent linking group.
- R 44 and R 45 represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyl group, or a heterocyclic group.
- M 4 represents a single bond or a divalent linking group.
- Q 4 represents an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group. At least two of Q 4 , M 4 and R 44 may be bonded to form a ring.
- R 41 , R 42 and R 43 have the same meanings as R 51 , R 52 and R 53 in the general formula (V), and preferred ranges thereof are also the same.
- L 4 has the same meaning as L 5 in the general formula (V), and the preferred range is also the same.
- R 44 and R 45 have the same meaning as R 3 in the general formula (3), and the preferred range is also the same.
- M 4 has the same meaning as M 3 in the general formula (3), and the preferred range is also the same.
- Q 4 has the same meaning as Q 3 in the general formula (3), and the preferred range is also the same.
- Examples of the ring formed by combining at least two of Q 4 , M 4 and R 44 include rings formed by combining at least two of Q 3 , M 3 and R 3 , and the preferred range is the same. It is. Specific examples of the repeating unit represented by the general formula (4) are shown below, but the present invention is not limited thereto.
- the resin (A) may contain a repeating unit represented by the following general formula (BZ).
- AR represents an aryl group.
- Rn represents an alkyl group, a cycloalkyl group, or an aryl group.
- Rn and AR may be bonded to each other to form a non-aromatic ring.
- R 1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group or an alkyloxycarbonyl group.
- repeating unit represented by the general formula (BZ) are shown below, but are not limited thereto.
- the above repeating unit having an acid-decomposable group may be one type or a combination of two or more types.
- the content of the repeating unit having an acid-decomposable group in the resin (A) (when there are a plurality of types) is 5 mol% or more and 80 mol% or less with respect to all the repeating units in the resin (A). It is preferably 5 mol% or more and 75 mol% or less, more preferably 10 mol% or more and 65 mol% or less.
- Resin (A) may contain a repeating unit represented by the following general formula (V) or the following general formula (VI).
- R 6 and R 7 are each independently a hydrogen atom, a hydroxy group, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, an alkoxy group or an acyloxy group, a cyano group, a nitro group, an amino group ,
- n 3 represents an integer of 0 to 6.
- n 4 represents an integer of 0 to 4.
- X 4 is a methylene group, an oxygen atom or a sulfur atom.
- Specific examples of the repeating unit represented by the general formula (V) or the general formula (VI) are shown below, but are not limited thereto.
- Resin (A) may further have a repeating unit having a silicon atom in the side chain.
- the repeating unit having a silicon atom in the side chain include a (meth) acrylate repeating unit having a silicon atom, a vinyl repeating unit having a silicon atom, and the like.
- the repeating unit having a silicon atom in the side chain is typically a repeating unit having a group having a silicon atom in the side chain. Examples of the group having a silicon atom include a trimethylsilyl group, a triethylsilyl group, and triphenyl.
- Silyl group tricyclohexylsilyl group, tristrimethylsiloxysilyl group, tristrimethylsilylsilyl group, methylbistrimethylsilylsilyl group, methylbistrimethylsiloxysilyl group, dimethyltrimethylsilylsilyl group, dimethyltrimethylsiloxysilyl group, Examples include a linear polysiloxane, a cage type, a ladder type, or a random type silsesquioxane structure.
- R and R1 each independently represent a monovalent substituent. * Represents a bond.
- the repeating unit having the above group can preferably include, for example, a repeating unit derived from an acrylate or methacrylate compound having the above group, or a repeating unit derived from a compound having the above group and a vinyl group. .
- the repeating unit having a silicon atom is preferably a repeating unit having a silsesquioxane structure, whereby it is ultrafine (for example, a line width of 50 nm or less), and the cross-sectional shape has a high aspect ratio (for example, In the formation of a pattern having a film thickness / line width of 3 or more, a very excellent collapse performance can be exhibited.
- the silsesquioxane structure include a cage-type silsesquioxane structure, a ladder-type silsesquioxane structure (ladder-type silsesquioxane structure), a random-type silsesquioxane structure, and the like.
- the cage silsesquioxane structure is a silsesquioxane structure having a cage structure.
- the cage silsesquioxane structure may be a complete cage silsesquioxane structure or an incomplete cage silsesquioxane structure, but may be a complete cage silsesquioxane structure.
- the ladder-type silsesquioxane structure is a silsesquioxane structure having a ladder-like skeleton.
- the random silsesquioxane structure is a silsesquioxane structure having a random skeleton.
- the cage silsesquioxane structure is preferably a siloxane structure represented by the following formula (S).
- R represents a monovalent organic group.
- a plurality of R may be the same or different.
- the organic group is not particularly limited, and specific examples thereof include a hydroxy group, a nitro group, a carboxy group, an alkoxy group, an amino group, a mercapto group, and a blocked mercapto group (for example, a mercapto group blocked (protected) with an acyl group) ), An acyl group, an imide group, a phosphino group, a phosphinyl group, a silyl group, a vinyl group, a hydrocarbon group optionally having a hetero atom, a (meth) acryl group-containing group, an epoxy group-containing group, and the like.
- hetero atom of the hydrocarbon group that may have a hetero atom examples include an oxygen atom, a nitrogen atom, a sulfur atom, and a phosphorus atom.
- hydrocarbon group of the hydrocarbon group that may have a heteroatom examples include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group in which these are combined.
- the aliphatic hydrocarbon group may be linear, branched or cyclic. Specific examples of the aliphatic hydrocarbon group include a linear or branched alkyl group (particularly 1 to 30 carbon atoms), a linear or branched alkenyl group (particularly 2 to 30 carbon atoms), And linear or branched alkynyl groups (particularly, having 2 to 30 carbon atoms).
- aromatic hydrocarbon group examples include aromatic hydrocarbon groups having 6 to 18 carbon atoms such as a phenyl group, a tolyl group, a xylyl group, and a naphthyl group.
- the content thereof is preferably 1 to 30 mol% with respect to all repeating units in the resin (A), and 5 to 25 mol%. Is more preferably 5 to 20 mol%.
- the actinic ray-sensitive or radiation-sensitive resin composition preferably contains a compound that generates an acid by actinic rays or radiation (hereinafter also referred to as “photo acid generator ⁇ PAG: Photo Acid Generator”).
- the photoacid generator may be in the form of a low molecular compound or may be incorporated in a part of the polymer. Moreover, you may use together the form incorporated in a part of polymer and the form of a low molecular compound.
- the photoacid generator is in the form of a low molecular compound, the molecular weight is preferably 3000 or less, more preferably 2000 or less, and even more preferably 1000 or less.
- the photoacid generator When the photoacid generator is in a form incorporated in a part of the polymer, it may be incorporated in a part of the resin (A) or in a resin different from the resin (A). In the present invention, the photoacid generator is preferably in the form of a low molecular compound.
- the photoacid generator is not particularly limited as long as it is a known one, but upon irradiation with actinic rays or radiation, preferably electron beams or extreme ultraviolet rays, an organic acid such as sulfonic acid, bis (alkylsulfonyl) imide, or Compounds that generate at least one of tris (alkylsulfonyl) methides are preferred. More preferred examples include compounds represented by the following general formula (ZI), (ZII), or (ZIII).
- R 201 , R 202 and R 203 each independently represents an organic group.
- the organic group as R 201 , R 202 and R 203 generally has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms.
- Two of R 201 to R 203 may be bonded to form a ring structure, and the ring may contain an oxygen atom, a sulfur atom, an ester bond, an amide bond, or a carbonyl group.
- Examples of the group formed by combining two members out of R 201 to R 203 include an alkylene group (eg, butylene group, pentylene group).
- Z ⁇ represents a non-nucleophilic anion (an anion having an extremely low ability to cause a nucleophilic reaction).
- non-nucleophilic anion examples include a sulfonate anion (such as an aliphatic sulfonate anion, an aromatic sulfonate anion, and a camphor sulfonate anion), a carboxylate anion (an aliphatic carboxylate anion, an aromatic carboxylate anion, And aralkylcarboxylate anions), sulfonylimide anions, bis (alkylsulfonyl) imide anions, tris (alkylsulfonyl) methide anions, and the like.
- a sulfonate anion such as an aliphatic sulfonate anion, an aromatic sulfonate anion, and a camphor sulfonate anion
- carboxylate anion an aliphatic carboxylate anion, an aromatic carboxylate anion, And aralkylcarboxylate anions
- the aliphatic moiety in the aliphatic sulfonate anion and aliphatic carboxylate anion may be an alkyl group or a cycloalkyl group, preferably a linear or branched alkyl group having 1 to 30 carbon atoms and a carbon number. Examples include 3 to 30 cycloalkyl groups.
- the aromatic group in the aromatic sulfonate anion and aromatic carboxylate anion is preferably an aryl group having 6 to 14 carbon atoms, such as a phenyl group, a tolyl group, and a naphthyl group.
- the alkyl group, cycloalkyl group and aryl group mentioned above may have a substituent. Specific examples thereof include nitro groups, halogen atoms such as fluorine atoms, carboxyl groups, hydroxyl groups, amino groups, cyano groups, alkoxy groups (preferably having 1 to 15 carbon atoms), cycloalkyl groups (preferably having 3 to 15 carbon atoms). ), An aryl group (preferably 6 to 14 carbon atoms), an alkoxycarbonyl group (preferably 2 to 7 carbon atoms), an acyl group (preferably 2 to 12 carbon atoms), an alkoxycarbonyloxy group (preferably 2 to 2 carbon atoms).
- an alkylthio group preferably having 1 to 15 carbon atoms
- an alkylsulfonyl group preferably having 1 to 15 carbon atoms
- an alkyliminosulfonyl group preferably having 1 to 15 carbon atoms
- an aryloxysulfonyl group preferably having carbon atoms Number 6 to 20
- alkylaryloxysulfonyl group preferably having 7 to 20 carbon atoms
- cycloalkylaryl Examples include a xysulfonyl group (preferably having 10 to 20 carbon atoms), an alkyloxyalkyloxy group (preferably having 5 to 20 carbon atoms), a cycloalkylalkyloxyalkyloxy group (preferably having 8 to 20 carbon atoms), and the like. it can.
- examples of the substituent further include an alkyl group (preferably having a carbon number of 1 to 15).
- the aralkyl group in the aralkyl carboxylate anion is preferably an aralkyl group having 7 to 12 carbon atoms, such as a benzyl group, a phenethyl group, a naphthylmethyl group, a naphthylethyl group, and a naphthylbutyl group.
- Examples of the sulfonylimide anion include saccharin anion.
- the alkyl group in the bis (alkylsulfonyl) imide anion and tris (alkylsulfonyl) methide anion is preferably an alkyl group having 1 to 5 carbon atoms.
- substituents for these alkyl groups include halogen atoms, alkyl groups substituted with halogen atoms, alkoxy groups, alkylthio groups, alkyloxysulfonyl groups, aryloxysulfonyl groups, and cycloalkylaryloxysulfonyl groups.
- a fluorine atom or an alkyl group substituted with a fluorine atom is preferred.
- the alkyl groups in the bis (alkylsulfonyl) imide anion may be bonded to each other to form a ring structure. This increases the acid strength.
- non-nucleophilic anions examples include fluorinated phosphorus (eg, PF 6 ⁇ ), fluorinated boron (eg, BF 4 ⁇ ), and fluorinated antimony (eg, SbF 6 ⁇ ). it can.
- non-nucleophilic anion examples include an aliphatic sulfonate anion in which at least ⁇ -position of the sulfonic acid is substituted with a fluorine atom, an aromatic sulfonate anion substituted with a fluorine atom or a group having a fluorine atom, and an alkyl group having a fluorine atom
- a bis (alkylsulfonyl) imide anion substituted with a tris (alkylsulfonyl) methide anion in which an alkyl group is substituted with a fluorine atom is preferred.
- the non-nucleophilic anion is more preferably a perfluoroaliphatic sulfonate anion (more preferably 4 to 8 carbon atoms) or a benzenesulfonate anion having a fluorine atom, and even more preferably a nonafluorobutanesulfonate anion.
- the pKa of the generated acid is preferably ⁇ 1 or less in order to improve sensitivity.
- an anion represented by the following general formula (AN1) can be mentioned as a preferred embodiment.
- Xf each independently represents a fluorine atom or an alkyl group substituted with at least one fluorine atom.
- R 1 and R 2 each independently represents a hydrogen atom, a fluorine atom, or an alkyl group, and when there are a plurality of R 1 and R 2 , R 1 and R 2 may be the same or different.
- L represents a divalent linking group, and when there are a plurality of L, L may be the same or different.
- A represents a cyclic organic group.
- x represents an integer of 1 to 20
- y represents an integer of 0 to 10
- z represents an integer of 0 to 10.
- the alkyl group in the alkyl group substituted with the fluorine atom of Xf preferably has 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms.
- the alkyl group substituted with a fluorine atom of Xf is preferably a perfluoroalkyl group.
- Xf is preferably a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms.
- Xf include fluorine atom, CF 3 , C 2 F 5 , C 3 F 7 , C 4 F 9 , CH 2 CF 3 , CH 2 CH 2 CF 3 , CH 2 C 2 F 5 , CH 2 CH 2 C 2 F 5 , CH 2 C 3 F 7 , CH 2 CH 2 C 3 F 7 , CH 2 C 4 F 9 , and CH 2 CH 2 C 4 F 9 are mentioned, among which fluorine atom and CF 3 are preferable. In particular, it is preferable that both Xf are fluorine atoms.
- the alkyl group of R 1 and R 2 may have a substituent (preferably a fluorine atom), and preferably has 1 to 4 carbon atoms. More preferred is a perfluoroalkyl group having 1 to 4 carbon atoms. Specific examples of the alkyl group having a substituent for R 1 and R 2 include CF 3 , C 2 F 5 , C 3 F 7 , C 4 F 9 , C 5 F 11 , C 6 F 13 , and C 7 F.
- R 1 and R 2 are preferably a fluorine atom or CF 3 .
- x is preferably from 1 to 10, and more preferably from 1 to 5.
- y is preferably 0 to 4, more preferably 0.
- z is preferably 0 to 5, and more preferably 0 to 3.
- the divalent linking group of L is not particularly limited, and is —COO—, —OCO—, —CO—, —O—, —S—, —SO—, —SO 2 —, an alkylene group, a cycloalkylene group, An alkenylene group, a linking group in which a plurality of these groups are linked, and the like can be exemplified, and a linking group having 12 or less carbon atoms is preferred.
- —COO—, —OCO—, —CO—, or —O— is preferable, and —COO— or —OCO— is more preferable.
- combinations of partial structures other than A include SO 3 —CF 2 —CH 2 —OCO—, SO 3 —CF 2 —CHF—CH 2 —OCO—, and SO 3 —CF. 2 -COO-, SO 3- -CF 2 -CF 2 -CH 2 -, or, SO 3- -CF 2 -CH (CF 3) -OCO- are mentioned as preferred.
- the cyclic organic group of A is not particularly limited as long as it has a cyclic structure, and includes an alicyclic group, an aryl group, and a heterocyclic group (not only those having aromaticity but also aromaticity). And the like).
- the alicyclic group may be monocyclic or polycyclic, and is a monocyclic cycloalkyl group such as a cyclopentyl group, a cyclohexyl group, and a cyclooctyl group; a norbornyl group, a tricyclodecanyl group, a tetracyclodecanyl group, a tetra
- a polycyclic cycloalkyl group such as a cyclododecanyl group and an adamantyl group is preferred.
- an alicyclic group having a bulky structure having 7 or more carbon atoms such as a norbornyl group, a tricyclodecanyl group, a tetracyclodecanyl group, a tetracyclododecanyl group, and an adamantyl group is used in the post-exposure heating step. It is preferable from the viewpoint of improving MEEF (mask error enhancement factor) because diffusibility in the film can be suppressed.
- the aryl group include a benzene ring, a naphthalene ring, a phenanthrene ring, and an anthracene ring.
- heterocyclic group examples include those derived from a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, and a pyridine ring. Of these, those derived from a furan ring, a thiophene ring, or a pyridine ring are preferred.
- examples of the cyclic organic group include lactone structures, and specific examples include lactone structures represented by the following general formulas (LC1-1) to (LC1-17).
- the cyclic organic group may have a substituent, and the substituent may be an alkyl group (which may be linear, branched, or cyclic, and preferably has 1 to 12 carbon atoms), A cycloalkyl group (which may be monocyclic, polycyclic or spirocyclic, preferably having 3 to 20 carbon atoms), an aryl group (preferably having 6 to 14 carbon atoms), a hydroxy group, an alkoxy group or an ester group Amide group, urethane group, ureido group, thioether group, sulfonamide group, sulfonic acid ester group and the like.
- the carbon constituting the cyclic organic group may be a carbonyl carbon.
- n2 represents an integer of 0 to 4.
- n2 is 2 or more, a plurality of Rb 2 may be the same or different, and a plurality of Rb 2 may be bonded to form a ring.
- examples of the organic group represented by R 201 , R 202, and R 203 include an aryl group, an alkyl group, and a cycloalkyl group.
- R 201 , R 202 and R 203 at least one is preferably an aryl group, more preferably all three are aryl groups.
- a heteroaryl group such as an indole residue and a pyrrole residue can be used.
- Preferred examples of the alkyl group and cycloalkyl group represented by R 201 to R 203 include a linear or branched alkyl group having 1 to 10 carbon atoms and a cycloalkyl group having 3 to 10 carbon atoms.
- a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, or the like is preferable.
- As the cycloalkyl group a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group is preferable.
- These groups may further have a substituent.
- substituents include nitro groups, halogen atoms such as fluorine atoms, carboxyl groups, hydroxyl groups, amino groups, cyano groups, alkoxy groups (preferably having 1 to 15 carbon atoms), cycloalkyl groups (preferably having 3 to 15 carbon atoms). ), An aryl group (preferably 6 to 14 carbon atoms), an alkoxycarbonyl group (preferably 2 to 7 carbon atoms), an acyl group (preferably 2 to 12 carbon atoms), and an alkoxycarbonyloxy group (preferably 2 carbon atoms). To 7), but is not limited thereto.
- R 204 to R 207 each independently represents an aryl group, an alkyl group, or a cycloalkyl group.
- the aryl group for R 204 to R 207 is preferably a phenyl group or a naphthyl group, and more preferably a phenyl group.
- the aryl group represented by R 204 to R 207 may be an aryl group having a heterocyclic structure having an oxygen atom, a nitrogen atom, a sulfur atom, or the like.
- Examples of the skeleton of the aryl group having a heterocyclic structure include pyrrole, furan, thiophene, indole, benzofuran, and benzothiophene.
- Examples of the alkyl group and cycloalkyl group in R 204 to R 207 include straight or branched alkyl groups having 1 to 10 carbon atoms (for example, methyl group, ethyl group, propyl group, butyl group, and pentyl group), or A cycloalkyl group having 3 to 10 carbon atoms (cyclopentyl group, cyclohexyl group, and norbornyl group) is preferable.
- the aryl group, alkyl group, and cycloalkyl group of R 204 to R 207 may have a substituent.
- substituents that the aryl group, alkyl group, and cycloalkyl group of R 204 to R 207 may have include, for example, an alkyl group (for example, 1 to 15 carbon atoms), a cycloalkyl group (for example, 3 to 3 carbon atoms). 15), aryl groups (for example, having 6 to 15 carbon atoms), alkoxy groups (for example, having 1 to 15 carbon atoms), halogen atoms, hydroxyl groups, and phenylthio groups.
- Z ⁇ represents a non-nucleophilic anion. Specifically, it is the same as that described as Z ⁇ in the general formula (ZI), and the preferred form is also the same.
- the photoacid generator has a volume of 130 to 3 or more by irradiation with an electron beam or extreme ultraviolet rays from the viewpoint of suppressing the diffusion of the acid generated by exposure to the non-exposed portion and improving the resolution.
- the volume is preferably 2000 3 or less, and more preferably 1500 3 or less.
- the volume value was determined using “WinMOPAC” manufactured by Fujitsu Limited. That is, first, the chemical structure of the acid according to each example is input, and then the most stable conformation of each acid is determined by molecular force field calculation using the MM3 method with this structure as the initial structure.
- the “accessible volume” of each acid can be calculated. 1 ⁇ means 0.1 nm.
- the calculated value of the volume is appended to a part of the example (unit 3 3 ).
- required here is a volume value of the acid which the proton couple
- Examples of the photoacid generator include paragraphs [0368] to [0377] of JP-A-2014-41328, and paragraphs [0240] to [0262] of JP-A-2013-228881 (corresponding US Patent Application Publication No. 2015/004533). No. [0339]), which is incorporated herein by reference. Moreover, although the following compounds are mentioned as a preferable specific example, it is not limited to these.
- a photo-acid generator can be used individually by 1 type or in combination of 2 or more types.
- the content of the photoacid generator in the actinic ray-sensitive or radiation-sensitive resin composition is preferably 0.1 to 50% by mass, more preferably 5 to 50% by mass, based on the total solid content of the composition. More preferably, it is 8 to 40% by mass.
- the content of the photoacid generator is preferably higher, more preferably 10 to 40% by mass, and still more preferably 10%. Is 35% by mass.
- (C) Solvent When preparing the actinic ray-sensitive or radiation-sensitive resin composition by dissolving the above-described components, a solvent can be used.
- the solvent that can be used include alkylene glycol monoalkyl ether carboxylate, alkylene glycol monoalkyl ether, alkyl lactate ester, alkyl alkoxypropionate, cyclic lactone having 4 to 10 carbon atoms, and ring having 4 to 10 carbon atoms.
- examples thereof may include organic solvents such as monoketone compounds, alkylene carbonates, alkyl alkoxyacetates, and alkyl pyruvates.
- alkylene glycol monoalkyl ether carboxylate examples include propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol monomethyl ether propionate, propylene glycol monoethyl Ether propionate, ethylene glycol monomethyl ether acetate, or ethylene glycol monoethyl ether acetate is preferred.
- alkylene glycol monoalkyl ether for example, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, ethylene glycol monomethyl ether, or ethylene glycol monoethyl ether is preferable.
- lactate alkyl ester for example, methyl lactate, ethyl lactate, propyl lactate, or butyl lactate is preferable.
- alkyl alkoxypropionate for example, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, methyl 3-ethoxypropionate, or ethyl 3-methoxypropionate is preferable.
- Examples of the cyclic lactone having 4 to 10 carbon atoms include ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -butyrolactone, ⁇ -methyl- ⁇ -butyrolactone, ⁇ -methyl- ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ - Caprolactone, ⁇ -octanoic lactone, or ⁇ -hydroxy- ⁇ -butyrolactone is preferred.
- Examples of the monoketone compound having 4 to 10 carbon atoms and optionally containing a ring include 2-butanone, 3-methylbutanone, pinacolone, 2-pentanone, 3-pentanone, 3-methyl-2-pentanone, 4- Methyl-2-pentanone, 2-methyl-3-pentanone, 4,4-dimethyl-2-pentanone, 2,4-dimethyl-3-pentanone, 2,2,4,4-tetramethyl-3-pentanone, 2 -Hexanone, 3-hexanone, 5-methyl-3-hexanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-methyl-3-heptanone, 5-methyl-3-heptanone, 2,6-dimethyl-4 -Heptanone, 2-octanone, 3-octanone, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 3-decanone, 4-decanone, 5- Xen-2-one, 3-
- alkylene carbonate for example, propylene carbonate, vinylene carbonate, ethylene carbonate, or butylene carbonate is preferable.
- alkyl alkoxyacetate examples include 2-methoxyethyl acetate, 2-ethoxyethyl acetate, 2- (2-ethoxyethoxy) ethyl acetate, 3-methoxy-3-methylbutyl acetate, and 1-methoxy-acetate. 2-propyl is preferred.
- alkyl pyruvate for example, methyl pyruvate, ethyl pyruvate, or propyl pyruvate is preferable.
- a solvent which can be preferably used a solvent having a boiling point of 130 ° C. or higher under normal temperature and normal pressure can be mentioned.
- the above solvents may be used alone or in combination of two or more.
- the solvent containing a hydroxyl group include ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, and ethyl lactate. Of these, propylene glycol monomethyl ether or ethyl lactate is preferable.
- Examples of the solvent not containing a hydroxyl group include propylene glycol monomethyl ether acetate, ethyl ethoxypropionate, 2-heptanone, ⁇ -butyrolactone, cyclohexanone, butyl acetate, N-methylpyrrolidone, N, N-dimethylacetamide, and dimethyl sulfoxide.
- propylene glycol monomethyl ether acetate, ethyl ethoxypropionate, 2-heptanone, ⁇ -butyrolactone, cyclohexanone, or butyl acetate are preferable.
- Propylene glycol monomethyl ether acetate, ethyl ethoxypropio Nate or 2-heptanone is more preferred.
- the mixing ratio (mass) of the solvent containing a hydroxyl group and the solvent not containing a hydroxyl group is preferably 1/99 to 99/1, more preferably 10/90 to 90/10, still more preferably 20/80 to 60 /. 40.
- a mixed solvent containing 50% by mass or more of a solvent not containing a hydroxyl group is particularly preferred from the viewpoint of coating uniformity.
- the solvent is preferably a mixed solvent of two or more containing propylene glycol monomethyl ether acetate.
- the solvent for example, the solvents described in JP-A-2014-219664, paragraphs 0013 to 0029 can also be used.
- the actinic ray-sensitive or radiation-sensitive resin composition preferably contains (E) a basic compound in order to reduce the change in performance over time from exposure to heating.
- a basic compound in order to reduce the change in performance over time from exposure to heating.
- Preferred examples of the basic compound include compounds having a structure represented by the following formulas (A) to (E).
- R 200 , R 201 and R 202 may be the same or different, and are a hydrogen atom, an alkyl group (preferably having a carbon number of 1 to 20), a cycloalkyl group (preferably a carbon atom). 3 to 20) or an aryl group (preferably having 6 to 20 carbon atoms), wherein R 201 and R 202 may be bonded to each other to form a ring.
- the alkyl group having a substituent is preferably an aminoalkyl group having 1 to 20 carbon atoms, a hydroxyalkyl group having 1 to 20 carbon atoms, or a cyanoalkyl group having 1 to 20 carbon atoms.
- R 203 , R 204 , R 205 and R 206 may be the same or different and each represents an alkyl group having 1 to 20 carbon atoms.
- the alkyl groups in the general formulas (A) and (E) are more preferably unsubstituted.
- Preferred compounds include guanidine, aminopyrrolidine, pyrazole, pyrazoline, piperazine, aminomorpholine, aminoalkylmorpholine, and piperidine, as well as imidazole structure, diazabicyclo structure, onium hydroxide structure, onium carboxylate structure, trialkylamine structure, Examples thereof include a compound having an aniline structure or a pyridine structure, an alkylamine derivative having a hydroxyl group and / or an ether bond, and an aniline derivative having a hydroxyl group and / or an ether bond.
- Examples of the compound having an imidazole structure include imidazole, 2,4,5-triphenylimidazole, and benzimidazole.
- Examples of the compound having a diazabicyclo structure include 1,4-diazabicyclo [2,2,2] octane, 1,5-diazabicyclo [4,3,0] non-5-ene, and 1,8-diazabicyclo [5,4, 0] undec-7-ene and the like.
- Examples of the compound having an onium hydroxide structure include triarylsulfonium hydroxide, phenacylsulfonium hydroxide, and sulfonium hydroxide having a 2-oxoalkyl group.
- triphenylsulfonium hydroxide tris (t- Butylphenyl) sulfonium hydroxide, bis (t-butylphenyl) iodonium hydroxide, phenacylthiophenium hydroxide, 2-oxopropylthiophenium hydroxide, and the like.
- the compound having an onium carboxylate structure is a compound having an onium hydroxide structure in which the anion moiety is converted to a carboxylate, and examples thereof include acetate, adamantane-1-carboxylate, and perfluoroalkylcarboxylate.
- Examples of the compound having a trialkylamine structure include tri (n-butyl) amine and tri (n-octyl) amine.
- Examples of aniline compounds include 2,6-diisopropylaniline, N, N-dimethylaniline, N, N-dibutylaniline, N, N-dihexylaniline, and the like.
- Examples of the alkylamine derivative having a hydroxyl group and / or an ether bond include ethanolamine, diethanolamine, triethanolamine, and tris (methoxyethoxyethyl) amine.
- Examples of aniline derivatives having a hydroxyl group and / or an ether bond include N, N-bis (hydroxyethyl) aniline.
- Preferred examples of the basic compound further include an amine compound having a phenoxy group and an ammonium salt compound having a phenoxy group.
- any of primary, secondary, and tertiary amine compounds can be used, and an amine compound in which at least one alkyl group is bonded to a nitrogen atom is preferable.
- the amine compound is more preferably a tertiary amine compound.
- the amine compound has an cycloalkyl group (preferably having 3 to 20 carbon atoms) or an aryl group (preferably having 3 to 20 carbon atoms).
- Preferably 6 to 12 carbon atoms may be bonded to the nitrogen atom.
- the amine compound preferably has an oxygen atom in the alkyl chain and an oxyalkylene group is formed.
- the number of oxyalkylene groups is one or more in the molecule, preferably 3 to 9, more preferably 4 to 6.
- an oxyethylene group (—CH 2 CH 2 O—) or an oxypropylene group (—CH (CH 3 ) CH 2 O— or —CH 2 CH 2 CH 2 O—) is preferable, and more preferable.
- ammonium salt compound any of primary, secondary, tertiary and quaternary ammonium salt compounds can be used, and an ammonium salt compound in which at least one alkyl group is bonded to a nitrogen atom is preferable.
- the ammonium salt compound may be a cycloalkyl group (preferably having 3 to 20 carbon atoms) or an aryl group, provided that at least one alkyl group (preferably having 1 to 20 carbon atoms) is bonded to the nitrogen atom. (Preferably having 6 to 12 carbon atoms) may be bonded to a nitrogen atom.
- the ammonium salt compound preferably has an oxygen atom in the alkyl chain and an oxyalkylene group is formed.
- the number of oxyalkylene groups is one or more in the molecule, preferably 3 to 9, more preferably 4 to 6.
- an oxyethylene group (—CH 2 CH 2 O—) or an oxypropylene group (—CH (CH 3 ) CH 2 O— or —CH 2 CH 2 CH 2 O—) is preferable, and more preferable. It is an oxyethylene group.
- the anion of the ammonium salt compound include a halogen atom, a sulfonate, a borate, and a phosphate. Among them, a halogen atom or a sulfonate is preferable.
- the halogen atom is preferably chloride, bromide or iodide
- the sulfonate is preferably an organic sulfonate having 1 to 20 carbon atoms.
- the organic sulfonate include alkyl sulfonates having 1 to 20 carbon atoms and aryl sulfonates.
- the alkyl group of the alkyl sulfonate may have a substituent, and examples of the substituent include fluorine, chlorine, bromine, alkoxy groups, acyl groups, and aryl groups.
- alkyl sulfonate examples include methane sulfonate, ethane sulfonate, butane sulfonate, hexane sulfonate, octane sulfonate, benzyl sulfonate, trifluoromethane sulfonate, pentafluoroethane sulfonate, and nonafluorobutane sulfonate.
- aryl group of the aryl sulfonate include a benzene ring, a naphthalene ring, and an anthracene ring.
- the benzene ring, naphthalene ring and anthracene ring may have a substituent, and the substituent is preferably a linear or branched alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms.
- the linear or branched alkyl group and cycloalkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, t-butyl, n-hexyl, cyclohexyl, and the like. It is done.
- the other substituent include an alkoxy group having 1 to 6 carbon atoms, a halogen atom, cyano, nitro, an acyl group, and an acyloxy group.
- the amine compound having a phenoxy group and the ammonium salt compound having a phenoxy group are those having a phenoxy group at the terminal opposite to the nitrogen atom of the alkyl group of the amine compound or ammonium salt compound.
- the phenoxy group may have a substituent.
- the substituent of the phenoxy group include an alkyl group, an alkoxy group, a halogen atom, a cyano group, a nitro group, a carboxyl group, a carboxylic acid ester group, a sulfonic acid ester group, an aryl group, an aralkyl group, an acyloxy group, and an aryloxy group. Groups and the like.
- the substitution position of the substituent may be any of the 2-6 positions.
- the number of substituents may be any in the range of 1 to 5.
- oxyalkylene group between the phenoxy group and the nitrogen atom.
- the number of oxyalkylene groups is one or more in the molecule, preferably 3 to 9, more preferably 4 to 6.
- an oxyethylene group (—CH 2 CH 2 O—) or an oxypropylene group (—CH (CH 3 ) CH 2 O— or —CH 2 CH 2 CH 2 O—) is preferable, and more preferable. It is an oxyethylene group.
- the amine compound having a phenoxy group was reacted with a primary or secondary amine having a phenoxy group and a haloalkyl ether by heating, and then an aqueous solution of a strong base such as sodium hydroxide, potassium hydroxide, and tetraalkylammonium was added. Then, it can obtain by extracting with organic solvents, such as ethyl acetate and chloroform.
- a strong base such as sodium hydroxide, potassium hydroxide, and tetraalkylammonium
- an aqueous solution of a strong base such as sodium hydroxide, potassium hydroxide, or tetraalkylammonium is added, and then ethyl acetate is added. And extraction with an organic solvent such as chloroform.
- composition according to the present invention has a proton acceptor functional group as a basic compound, and is decomposed by irradiation with actinic rays or radiation, resulting in a decrease, disappearance, or a proton acceptor property. It may further contain a compound that generates a compound that has been changed to acidity (hereinafter also referred to as compound (PA)).
- PA acidic property
- the proton acceptor functional group is a functional group having electrons or a group capable of electrostatically interacting with protons, for example, a functional group having a macrocyclic structure such as a cyclic polyether, and a ⁇ conjugate. It means a functional group having a nitrogen atom with an unshared electron pair that does not contribute to.
- the nitrogen atom having an unshared electron pair that does not contribute to ⁇ conjugation is, for example, a nitrogen atom having a partial structure represented by the following general formula.
- Preferred partial structures of the proton acceptor functional group include, for example, crown ether, azacrown ether, primary to tertiary amines, pyridine, imidazole, and pyrazine structures.
- the compound (PA) is decomposed by irradiation with actinic rays or radiation to generate a compound whose proton acceptor property is lowered, disappeared, or changed from proton acceptor property to acidity.
- the decrease or disappearance of the proton acceptor property or the change from the proton acceptor property to the acid is a change in the proton acceptor property caused by the addition of a proton to the proton acceptor functional group.
- a proton adduct is formed from a compound having a proton acceptor functional group (PA) and a proton, the equilibrium constant in the chemical equilibrium is reduced.
- Specific examples of the compound (PA) include the following compounds. Furthermore, as specific examples of the compound (PA), for example, those described in paragraphs 0421 to 0428 of JP 2014-41328 A and paragraphs 0108 to 0116 of JP 2014-134686 A can be used. The contents of which are incorporated herein.
- the amount of the basic compound used is usually 0.001 to 10% by mass, preferably 0.01 to 5% by mass, based on the solid content of the actinic ray-sensitive or radiation-sensitive composition.
- the molar ratio is preferably 2.5 or more from the viewpoint of sensitivity and resolution, and is preferably 300 or less from the viewpoint of suppressing the reduction in resolution due to the thickening of the resist pattern over time until post-exposure heat treatment.
- the photoacid generator / basic compound (molar ratio) is more preferably from 5.0 to 200, still more preferably from 7.0 to 150.
- the actinic ray-sensitive or radiation-sensitive resin composition may have a hydrophobic resin (A ′) separately from the resin (A).
- the hydrophobic resin is preferably designed to be unevenly distributed on the surface of the resist film. However, unlike the surfactant, it is not always necessary to have a hydrophilic group in the molecule, and the polar / nonpolar substance is uniformly mixed. There is no need to contribute. Examples of the effect of adding the hydrophobic resin include control of the static / dynamic contact angle of the resist film surface with respect to water, suppression of outgas, and the like.
- the hydrophobic resin has at least one of “fluorine atom”, “silicon atom”, and “CH 3 partial structure contained in the side chain portion of the resin” from the viewpoint of uneven distribution in the film surface layer. It is preferable to have two or more types.
- the hydrophobic resin preferably contains a hydrocarbon group having 5 or more carbon atoms. These groups may be present in the main chain of the resin or may be substituted on the side chain.
- the fluorine atom and / or silicon atom in the hydrophobic resin may be contained in the main chain of the resin or in the side chain. It may be.
- the hydrophobic resin when it contains a fluorine atom, it may be a resin having an alkyl group having a fluorine atom, a cycloalkyl group having a fluorine atom, or an aryl group having a fluorine atom as a partial structure having a fluorine atom.
- the alkyl group having a fluorine atom preferably having 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms
- the cycloalkyl group having a fluorine atom is a monocyclic or polycyclic cycloalkyl group in which at least one hydrogen atom is substituted with a fluorine atom, and may further have a substituent other than a fluorine atom.
- the aryl group having a fluorine atom include those in which at least one hydrogen atom of an aryl group such as a phenyl group and a naphthyl group is substituted with a fluorine atom, and further a substituent other than a fluorine atom may be included.
- Examples of the repeating unit having a fluorine atom or a silicon atom include those exemplified in paragraph 0519 of US2012 / 0251948A1.
- the hydrophobic resin preferably includes a CH 3 partial structure in the side chain portion.
- the CH 3 partial structure contained in the side chain portion of the hydrophobic resin is intended to encompass CH 3 partial structure ethyl, and propyl groups and the like have.
- methyl groups directly bonded to the main chain of the hydrophobic resin for example, ⁇ -methyl groups of repeating units having a methacrylic acid structure
- hydrophobic resin those described in JP 2011-248019 A, JP 2010-175859 A, and JP 2012-032544 A can also be preferably used.
- the actinic ray-sensitive or radiation-sensitive resin composition may further contain a surfactant (F).
- a surfactant By containing a surfactant, when an exposure light source having a wavelength of 250 nm or less, particularly 220 nm or less, is used, it is possible to form a pattern with less adhesion and development defects with good sensitivity and resolution. Become.
- the surfactant it is particularly preferable to use a fluorine-based and / or silicon-based surfactant. Examples of the fluorine-based and / or silicon-based surfactant include surfactants described in [0276] of US Patent Application Publication No. 2008/0248425.
- F top EF301 or EF303 (manufactured by Shin-Akita Kasei Co., Ltd.); Florard FC430, 431 or 4430 (manufactured by Sumitomo 3M Co., Ltd.); Megafac F171, F173, F176, F189, F113, F110, F177, F120 or R08 (manufactured by DIC Corporation); Surflon S-382, SC101, 102, 103, 104, 105 or 106 (manufactured by Asahi Glass Co., Ltd.); Troisol S-366 (manufactured by Troy Chemical Co., Ltd.); GF-300 or GF-150 (manufactured by Toa Synthetic Chemical Co., Ltd.), Surflon S-393 (manufactured by Seimi Chemical Co., Ltd.); 01 (manufactured by Gemco); PF636, PF656, PF6320 or PF6520 (manufactured by OMNOVA); or
- the surfactant is a fluoroaliphatic compound produced by a telomerization method (also referred to as a telomer method) or an oligomerization method (also referred to as an oligomer method). You may synthesize. Specifically, a polymer having a fluoroaliphatic group derived from this fluoroaliphatic compound may be used as a surfactant. This fluoroaliphatic compound can be synthesized, for example, by the method described in JP-A-2002-90991. Further, surfactants other than fluorine-based and / or silicon-based surfactants described in [0280] of US Patent Application Publication No. 2008/0248425 may be used.
- surfactants may be used alone or in combination of two or more.
- the actinic ray-sensitive or radiation-sensitive resin composition contains a surfactant
- the content thereof is preferably 0 to 2% by mass, more preferably 0.0001, based on the total solid content of the composition. It is ⁇ 2 mass%, more preferably 0.0005 to 1 mass%.
- the actinic ray-sensitive or radiation-sensitive resin composition is a compound that promotes solubility in a dissolution inhibiting compound, dye, plasticizer, photosensitizer, light absorber, and / or developer.
- a phenol compound having a molecular weight of 1000 or less, an alicyclic or aliphatic compound containing a carboxy group, and the like may further be included.
- the actinic ray-sensitive or radiation-sensitive resin composition may further contain a dissolution inhibiting compound.
- the “dissolution inhibiting compound” is a compound having a molecular weight of 3000 or less, which is decomposed by the action of an acid to reduce the solubility in an organic developer.
- an upper layer film (top coat film) may be formed on the resist film. It is preferable that the upper layer film is not mixed with the resist film and can be uniformly applied to the upper layer of the resist film.
- the upper layer film is not particularly limited, and a conventionally known upper layer film can be formed by a conventionally known method.
- the upper layer film can be formed based on the description in paragraphs 0072 to 0082 of JP-A-2014-059543.
- a hydrophobic resin or the like can be used in addition to the polymer described in paragraph 0072 of JP-A-2014-059543.
- the hydrophobic resin for example, the above-described hydrophobic resin (A ′) can be used.
- a developer containing an organic solvent is used in the development step, for example, it is preferable to form an upper layer film containing a basic compound on the resist film as described in JP2013-61648A, for example.
- Specific examples of the basic compound that can be contained in the upper layer film include the basic compound (E) described above.
- the upper layer film preferably contains a compound containing at least one group or bond selected from the group consisting of an ether bond, a thioether bond, a hydroxyl group, a thiol group, a carbonyl bond and an ester bond.
- the upper layer film may contain a photoacid generator.
- photo-acid generator As a photo-acid generator, the thing similar to the photo-acid generator (for example, photo acid generator (B) mentioned above) which can be contained in actinic-ray-sensitive or radiation-sensitive composition can be used.
- the resin that is preferably used for the upper layer film (top coat film) will be described.
- the composition for forming an upper layer film preferably contains a resin.
- the resin that can be contained in the composition for forming an upper layer film is not particularly limited, but is a hydrophobic resin that can be included in the actinic ray-sensitive or radiation-sensitive composition (for example, the above-described hydrophobic resin (A ′)) ) Can be used.
- the hydrophobic resin [0017] to [0023] of JP2013-61647A (corresponding [0017] to [0023] of US Patent Publication No. 2013/244438) and JP2014-56194A. [0016] to [0165] can be referred to, the contents of which are incorporated herein.
- the composition for forming an upper layer film preferably contains a resin containing a repeating unit having an aromatic ring.
- a repeating unit having an aromatic ring By containing a repeating unit having an aromatic ring, the generation efficiency of secondary electrons and the efficiency of acid generation from a compound that generates an acid by actinic rays or radiation, particularly during electron beam or EUV exposure, are increased. High sensitivity and high resolution can be expected when forming
- the weight average molecular weight of the resin is preferably 3000 to 100,000, more preferably 3000 to 30000, and still more preferably 5000 to 20000.
- the amount of the resin in the composition for forming the upper layer film is preferably 50 to 99.9% by mass, more preferably 60 to 99.0% by mass, and still more preferably 70 to 99.7% by mass in the total solid content. 80 to 99.5% by mass is even more preferable.
- topcoat composition When the composition for forming an upper layer film (topcoat composition) includes a plurality of resins, it is preferable to include at least one resin (XA) having a fluorine atom and / or a silicon atom.
- the preferred range of the content of fluorine atoms and silicon atoms contained in the resin (XA) is preferably such that the repeating unit containing fluorine atoms and / or silicon atoms is 10 to 100% by mass in the resin (XA), More preferably, it is 10 to 99 mol%, and still more preferably 20 to 80 mol%.
- the composition for forming an upper layer film includes at least one resin (XA) having a fluorine atom and / or a silicon atom, and a resin (XB) having a fluorine atom and / or silicon atom content smaller than that of the resin (XA). And more preferably.
- the resin (XA) is unevenly distributed on the surface of the upper layer film, so that performance such as development characteristics or immersion liquid followability can be further improved.
- the content of the resin (XA) is preferably 0.01 to 30% by mass, more preferably 0.1 to 10% by mass, based on the total solid content contained in the upper layer film-forming composition, 8% by mass is more preferable, and 0.1 to 5% by mass is particularly preferable.
- the content of the resin (XB) is preferably 50.0 to 99.9% by mass, more preferably 60 to 99.9% by mass, based on the total solid content contained in the composition for forming an upper layer film, and 70 to 99.9% by mass is more preferable, and 80 to 99.9% by mass is particularly preferable.
- the resin (XB) a form that substantially does not contain a fluorine atom and a silicon atom is preferable.
- the total content of the repeating unit having a fluorine atom and the repeating unit having a silicon atom is, It is preferably 0 to 20 mol%, more preferably 0 to 10 mol%, still more preferably 0 to 5 mol%, particularly preferably 0 to 3 mol%, ideally with respect to all repeating units in the resin (XB). Is 0 mol%, that is, does not contain fluorine atoms or silicon atoms.
- the composition for forming an upper layer film is preferably filtered by dissolving each component in a solvent.
- the filter is preferably made of polytetrafluoroethylene, polyethylene, or nylon having a pore size of 0.1 ⁇ m or less, more preferably 0.05 ⁇ m or less, and still more preferably 0.03 ⁇ m or less. Note that a plurality of types of filters may be connected in series or in parallel.
- the composition may be filtered a plurality of times, and the step of filtering a plurality of times may be a circulation filtration step. Furthermore, you may perform a deaeration process etc.
- the composition for forming an upper layer film does not contain impurities such as metals.
- the content of the metal component contained in these materials is preferably 10 ppm or less, more preferably 5 ppm or less, still more preferably 1 ppm or less, and particularly preferably (not more than the detection limit of the measuring device). .
- the upper layer film when the exposure is immersion exposure, the upper layer film is disposed between the actinic ray-sensitive or radiation-sensitive film and the immersion liquid, and the actinic ray-sensitive or radiation-sensitive film. It also functions as a layer that does not come into direct contact with the immersion liquid.
- preferable properties of the upper layer film include suitability for application to an actinic ray-sensitive or radiation-sensitive film, transparency to radiation, particularly 193 nm, and immersion liquid ( Preferably, it is sparingly soluble in water.
- the upper layer film is not mixed with the actinic ray-sensitive or radiation-sensitive film and can be uniformly applied to the surface of the actinic-ray-sensitive or radiation-sensitive film.
- the composition for forming the upper layer film is used.
- the solvent that does not dissolve the actinic ray-sensitive or radiation-sensitive film it is more preferable to use a solvent having a component different from that of a developer containing an organic solvent (organic developer).
- the coating method of the composition for forming the upper layer film is not particularly limited, and a conventionally known spin coating method, spray method, roller coating method, dipping method, and the like can be used.
- the thickness of the upper layer film is not particularly limited, but is usually 5 nm to 300 nm, preferably 10 nm to 300 nm, more preferably 20 nm to 200 nm, still more preferably 30 nm to 100 nm from the viewpoint of transparency to the exposure light source. .
- the substrate is heated (PB; PreBake) as necessary.
- the refractive index of the upper layer film is preferably close to the refractive index of the actinic ray-sensitive or radiation-sensitive film from the viewpoint of resolution.
- the upper layer film is preferably insoluble in the immersion liquid, and more preferably insoluble in water.
- the receding contact angle of the upper layer film is preferably 50 to 100 °, more preferably 80 to 100 °, from the viewpoint of immersion liquid followability. More preferred.
- immersion exposure the immersion head needs to move on the wafer following the movement of the exposure head to scan the wafer at high speed to form an exposure pattern.
- the contact angle of the immersion liquid with respect to the light-sensitive or radiation-sensitive film is important, and in order to obtain better resist performance, it is preferable to have a receding contact angle in the above range.
- an organic developer may be used, or a separate release agent may be used.
- a solvent having a small penetration into the actinic ray sensitive or radiation sensitive film is preferable.
- the upper layer film can be peeled off with an organic developer in that the upper layer film can be peeled off simultaneously with the development of the actinic ray-sensitive or radiation-sensitive film.
- the organic developer used for peeling is not particularly limited as long as it can dissolve and remove the low-exposed portion of the actinic ray-sensitive or radiation-sensitive film.
- the dissolution rate of the upper layer film in the organic developer is preferably 1 to 300 nm / sec, more preferably 10 to 100 nm / sec.
- the dissolution rate of the upper layer film with respect to the organic developer is a rate of film thickness reduction when the upper layer film is formed and then exposed to the developer.
- the film was immersed in butyl acetate at 23 ° C. Speed.
- the line edge of the pattern after developing the actinic ray-sensitive or radiation-sensitive film probably due to the effect of reducing the exposure unevenness during the immersion exposure. There is an effect that the roughness becomes better.
- the upper layer film may be removed using another known developer, for example, an alkaline aqueous solution.
- the aqueous alkali solution that can be used include an aqueous solution of tetramethylammonium hydroxide.
- compositions used in the actinic ray-sensitive or radiation-sensitive resin composition and the pattern forming method of the present invention for example, the processing liquid (for example, developer or rinsing liquid) of the present invention, resist solvent, reflection
- the composition for forming a prevention film, the composition for forming an upper layer film, etc. preferably does not contain impurities such as metals, metal salts containing halogens, acids, alkalis, sulfur-containing compounds, and phosphorus-containing compounds.
- the content of impurities contained in these materials is preferably 1 ppm or less, more preferably 1 ppb or less, still more preferably 100 ppt or less, particularly preferably 10 ppt or less, and substantially free (below the detection limit of the measuring device). Is most preferable.
- Examples of a method for removing impurities such as metals from the various materials include filtration using a filter.
- the pore size of the filter is preferably 10 nm or less, more preferably 5 nm or less, and still more preferably 3 nm or less.
- the filter material is preferably a polytetrafluoroethylene, polyethylene, or nylon filter.
- the filter may be a composite material obtained by combining these materials and ion exchange media.
- a filter that has been washed in advance with an organic solvent may be used.
- a plurality of types of filters may be connected in series or in parallel.
- filters having different pore diameters and / or materials may be used in combination.
- various materials may be filtered a plurality of times, and the step of filtering a plurality of times may be a circulating filtration step.
- a raw material having a low metal content is selected as a raw material constituting the various materials, and filter filtration is performed on the raw materials constituting the various materials.
- adsorbent known adsorbents can be used.
- inorganic adsorbents such as silica gel and zeolite, and organic adsorbents such as activated carbon can be used.
- the processing solution of the present invention such as a developing solution and a rinsing solution
- a container for storing a processing solution for patterning a chemically amplified resist film which has a storage part.
- the inner wall of the container in contact with the treatment liquid is subjected to a resin different from any of polyethylene resin, polypropylene resin, and polyethylene-polypropylene resin, or rust prevention or metal elution prevention treatment is performed.
- An organic solvent that is to be used as a chemical amplification resist film patterning treatment solution is stored in the storage portion of the storage container, and the one discharged from the storage portion is used when the chemical amplification resist film is patterned. can do.
- the seal portion is also selected from the group consisting of polyethylene resin, polypropylene resin, and polyethylene-polypropylene resin. It is preferably formed from a resin different from the resin, or a metal that has been subjected to rust prevention or metal elution prevention treatment.
- the seal part means a member capable of shutting off the accommodating part and the outside air, and can preferably include a packing, an O-ring and the like.
- the resin different from the resin selected from the group consisting of polyethylene resin, polypropylene resin, and polyethylene-polypropylene resin is preferably a perfluoro resin.
- Perfluoro resins include tetrafluoroethylene resin (PTFE), tetrafluoroethylene / perfluoroalkyl vinyl ether copolymer (PFA), tetrafluoroethylene-hexafluoropropylene copolymer resin (FEP), tetrafluoride.
- PTFE tetrafluoroethylene resin
- PFA perfluoroalkyl vinyl ether copolymer
- FEP tetrafluoroethylene-hexafluoropropylene copolymer resin
- Ethylene-ethylene copolymer resin Ethylene-ethylene copolymer resin (ETFE), ethylene trifluoride-ethylene copolymer resin (ECTFE), vinylidene fluoride resin (PVDF), ethylene trifluoride chloride copolymer resin (PCTFE), and vinyl fluoride Resin (PVF) etc.
- ETFE ethylene trifluoride-ethylene copolymer resin
- PVDF vinyli
- Particularly preferable perfluoro resins include tetrafluoroethylene resin, tetrafluoroethylene / perfluoroalkyl vinyl ether copolymer, and tetrafluoroethylene-hexafluoropropylene copolymer resin.
- Examples of the metal in the metal subjected to rust prevention or metal elution prevention treatment include carbon steel, alloy steel, nickel chrome steel, nickel chrome molybdenum steel, chrome steel, chrome molybdenum steel, and manganese steel.
- rust prevention or metal elution prevention treatment it is preferable to apply a coating technique.
- metal coating variant plating
- inorganic coating variant chemical conversion treatment, glass, concrete, ceramics, etc.
- organic coating rust prevention oil, paint, rubber, and plastics. It has been separated.
- Preferred film technology includes surface treatment with a rust inhibitor oil, a rust inhibitor, a corrosion inhibitor, a chelate compound, a peelable plastic, or a lining agent.
- corrosion inhibitors such as glycerin esters or phosphate esters
- chelating compounds such as ethylene diantetraacetic acid, gluconic acid, nitrilotriacetic acid, hydroxyethyl ethyl orange amine trisuccinic acid, and diethylene triamine pentonic acid
- fluororesin lining Particularly preferred are phosphating and fluororesin lining.
- pretreatment is a stage before rust prevention treatment. It is also preferable to adopt.
- a treatment for removing various corrosion factors such as chlorides and sulfates existing on the metal surface by washing or polishing can be preferably mentioned.
- the storage container include the following. ⁇ FluoroPure PFA composite drum manufactured by Entegris (Wetted inner surface; PFA resin lining) ⁇ JFE steel drums (wetted inner surface; zinc phosphate coating)
- Examples of the storage container include a storage container described in paragraphs 0013 to 0030 of JP-A-11-021393, a storage container described in paragraphs 0012 to 0024 of JP-A-10-45961, and the like.
- a conductive compound is added to prevent chemical piping and various parts (filters, O-rings, tubes, etc.) from being damaged due to electrostatic charging or subsequent electrostatic discharge. May be.
- the treatment liquid of the present invention contains a highly polar organic solvent having an SP value of 17.1 MPa 1/2 or more, it itself has an effect of suppressing electrostatic charge.
- the combined use with can further suppress electrostatic charging.
- limit especially as an electroconductive compound For example, methanol is mentioned.
- the addition amount is not particularly limited, but is preferably 10% by mass or less, more preferably 5% by mass or less from the viewpoint of maintaining preferable development characteristics.
- SUS or various pipes coated with polyethylene, polypropylene, or fluororesin (such as polytetrafluoroethylene and perfluoroalkoxy resin) subjected to antistatic treatment can be used.
- polyethylene, polypropylene, or fluororesin (polytetrafluoroethylene, perfluoroalkoxy resin, etc.) subjected to antistatic treatment can be used for the filter and O-ring.
- reaction solution was cooled to room temperature and dropped into 3 L of hexane to precipitate a polymer.
- the filtered solid was dissolved in 500 mL of acetone and dropped again into 3 L of hexane, and then the filtered solid was dried under reduced pressure to give 160 g of 4-acetoxystyrene / 1-ethylcyclopentyl methacrylate / monomer 1 copolymer (A-1a).
- the weight average molecular weight (Mw) in terms of standard polystyrene by gel permeation chromatography (GPC) was 11,200, and the molecular weight dispersity (Mw / Mn) was 1.45.
- Resins (A-2) to (A-19) and (A-21) to (A-23) having the structures shown in Table 3 were prepared in the same manner as in Synthesis Example 1 except that the monomers used were changed. ) was synthesized.
- the composition ratio (molar ratio) of the resin was calculated by 1 H-NMR (nuclear magnetic resonance) measurement.
- the weight average molecular weight (Mw: polystyrene conversion) and dispersity (Mw / Mn) of the resin were calculated by GPC (solvent: THF) measurement.
- the weight average molecular weight and dispersity of other resins shown in the examples were measured by the same method.
- Photoacid generator (B) As the photoacid generator, the following were used.
- ⁇ Resist composition> Each component shown in Table 5 below was dissolved in the solvent shown in the same table. This was filtered using a polyethylene filter having a pore size of 0.03 ⁇ m to obtain a resist composition.
- composition for forming upper layer film Each component shown in Table 6 below was dissolved in the solvent shown in the same table. This was filtered using a polyethylene filter having a pore size of 0.03 ⁇ m to obtain a composition for forming an upper layer film.
- MIBC represents methyl isobutyl carbinol.
- the resins V-1 to V-4, 1b and additive X1 used are shown below. Other additives are the same as those described above.
- the composition ratio, weight average molecular weight, and degree of dispersion of the resins V-1 to V-4 and 1b are shown in a separate table (Table 7).
- EUV exposure (Examples 1-1 to 1-44, Comparative Examples 1-1 to 1-7) ⁇ EUV exposure evaluation> A resist pattern was formed by the following operation using the resist composition described in Table 5.
- PB baking after application
- each resist composition obtained as described above was applied and baked for 60 seconds under the condition of 90 to 180 ° C. (see the PB column in Table 9) to form a resist film having a thickness of 40 nm.
- the resist composition 31 used in Example 1-24 is a positive resist composition, and in the other Examples and Comparative Examples, a negative resist composition was used.
- PEB Post-exposure bake
- the SP value of each developer / rinse solution is calculated using the Fedors method described in “Properties of Polymers, 2nd edition, 1976 publication” (unit: MPa 1 / 2 ).
- the "dielectric constant” is listed in “Handbook of Organic Solvent Properties, Ian M. Smallwood, 1996, Elsevier” and “CRC Handbook of Chemistry and Physics, 96th Edition, William M. Haynes, 2015, CRC Press”. The specified dielectric constant (mainly a value at a temperature of 20 ° C.) is used.
- the rinse process was performed by spraying a rinse liquid (23 degreeC) for 15 second by the flow volume of 200 mL / min, rotating a wafer by 50 rotations (rpm). Finally, the wafer was dried by high-speed rotation at 2500 rotations (rpm) for 60 seconds.
- a rinse liquid 23 degreeC
- SA-1 to SA-9 shown in Table 8 was used as the rinsing liquid.
- Table 9 shows the types of rinse solutions used in the examples and comparative examples.
- EUV exposure-double patterning (Example 1-45) [Application of resist composition and baking after application (PB)] An organic film DUV44 (manufactured by Brewer Science) was applied onto a 12-inch silicon wafer and baked at 200 ° C. for 60 seconds to form an organic film having a thickness of 60 nm. Resist composition 1 was applied thereon and baked at 90 ° C. for 60 seconds to form a resist film having a thickness of 60 nm.
- the wafer prepared above was subjected to EUV exposure with NA (Numerical Aperture) 0.25 and dipole illumination (Dipole 60x, outer sigma 0.81, inner sigma 0.43). Specifically, the first EUV exposure is performed through a mask having a 40 nm space and a 120 nm line pattern, and the mask is positioned in the middle of the first exposure space and the space with the same pattern as the first mask. The second exposure was performed with a shift of 80 nm so as to be arranged.
- NA Numerical Aperture
- dipole illumination Dipole 60x, outer sigma 0.81, inner sigma 0.43
- a mask with a half-pitch 30 nm line space is formed on the wafer produced above with NA (lens numerical aperture) 0.25, dipole illumination (X deflection, Dipole 60x, outer sigma 0.81, inner sigma 0.43) The first EUV exposure was performed. Thereafter, a second EUV exposure was performed using a mask having a half-pitch 30 nm line space with dipole illumination (Y deflection, Dipole 60y, outer sigma 0.81, inner sigma 0.43).
- An organic film DUV44 (manufactured by Brewer Science) was applied on a 6-inch silicon wafer and baked at 200 ° C. for 60 seconds to form an organic film having a thickness of 60 nm.
- a resist composition described in Table 5 was applied thereon, and baked for 60 seconds under the conditions of 90 to 180 ° C. (see the PB column in Table 10) to form a resist film having a thickness of 40 nm.
- the resist composition 31 used in Example 2-24 was a positive resist composition, and in the other Examples and Comparative Examples, a negative resist composition was used.
- PEB Post-exposure bake
- the rinse treatment was performed by spraying the rinse liquid (23 ° C.) at a flow rate of 200 mL / min for 15 seconds while rotating the wafer at 50 revolutions (rpm). Finally, the wafer was dried by high-speed rotation at 2500 rotations (rpm) for 60 seconds.
- the rinsing liquid any one of the processing liquids S-1 to S-20 and SA-1 to SA-9 shown in Table 8 was used. Table 10 shows the rinse solutions used in the examples and comparative examples.
- An organic antireflection film ARC29SR (manufactured by Brewer) is applied on an 8-inch silicon wafer, and baked at 205 ° C. for 60 seconds to form an antireflection film having a thickness of 86 nm, which is obtained as described above.
- Each of the obtained resist compositions was applied and baked for 60 seconds under the condition of 90 to 120 ° C. (see the PB column in Table 11) to form a resist film having a thickness of 40 nm.
- the SP value of at least one of the developing solution and the rinsing solution is 16.3 MPa 1/2 regardless of which exposure light source is used.
- the following first organic solvent and a second organic solvent having an SP value of 17.1 MPa 1/2 or more are contained, occurrence of pattern collapse in the resist L / S pattern and occurrence of defective omission in the resist C / H pattern It was found that can be suppressed simultaneously.
- the treatment liquid of the present invention can be applied to both a negative type resin and a positive type resin.
- the treatment liquid according to the present invention is applied to a FluoroPure PFA composite drum (wetted inner surface; PFA resin lining) manufactured by Entegris and a steel drum can (wetted inner surface; zinc phosphate coating) manufactured by JFE as described in JP-A-2014-112176.
- a FluoroPure PFA composite drum wetted inner surface; PFA resin lining
- a steel drum can wetted inner surface; zinc phosphate coating
- JFE wetted inner surface; zinc phosphate coating
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Abstract
Description
より詳細には、本発明は、IC(Integrated Circuit、集積回路)等の半導体製造工程、液晶及びサーマルヘッド等の回路基板の製造、さらにはその他のフォトファブリケーションのリソグラフィー工程等に使用される、処理液、及びパターン形成方法に関する。
このようなリソグラフィーにおいては、フォトレジスト組成物(感活性光線又は感放射線性組成物、又は、化学増幅型レジスト組成物とも呼ばれる)により膜を形成した後、得られた膜を現像液により現像したり、現像後の膜をリンス液で洗浄することが行われている。
例えば、特許文献1には、現像液として、ケトン系溶剤及びエステル系溶剤から選ばれる第一の有機溶剤と第二の有機溶剤の混合物を含有する有機系処理液を用いることが開示されている。
より具体的には、以下の構成により上記目的を達成することができることを見出した。
SP値が16.3MPa1/2以下の第一の有機溶剤とSP値が17.1MPa1/2以上の第二の有機溶剤を含有する、処理液。
(2) 上記処理液が、リンス液である、(1)に記載の処理液。
(3) 上記第一の有機溶剤が、炭化水素系溶剤を含む、(2)に記載の処理液。
(4) 上記第一の有機溶剤が、炭素数10以上の炭化水素系溶剤を含む、(3)に記載の処理液。
(5) 上記炭化水素系溶剤が、ウンデカンを含む、(3)又は(4)に記載の処理液。
(6) 上記第二の有機溶剤が、ケトン系溶剤を含む、(1)~(5)のいずれかに記載の処理液。
(7) 上記ケトン系溶剤が、非環状ケトンを含む、(6)に記載の処理液。
(8) 感活性光線又は感放射線性組成物を用いてレジスト膜を形成するレジスト膜形成工程と、
上記レジスト膜を露光する露光工程と、
露光された上記レジスト膜を(1)~(7)のいずれかに記載の処理液によって処理する処理工程と、を含む、パターン形成方法。
(9) 上記処理工程は、
現像液によって現像する現像工程と、
リンス液によって洗浄するリンス工程を備え、
上記リンス液が(1)~(7)のいずれかに記載の処理液である、(8)に記載のパターン形成方法。
(10) 上記現像液が、エステル系溶剤を含む、(9)に記載のパターン形成方法。
(11) 上記エステル系溶剤が、酢酸ブチル、酢酸アミル、酢酸イソアミル、酢酸2-メチルブチル、酢酸1-メチルブチル、酢酸ヘキシル、プロピオン酸ペンチル、プロピオン酸ヘキシル、プロピオン酸ヘプチル、ブタン酸ブチル、及びイソブタン酸ブチルからなる群から選ばれる少なくともいずれか1種を含む溶剤である、(10)に記載のパターン形成方法。
本発明の処理液は、感活性光線又は感放射線性組成物から得られるレジスト膜に対して現像及び洗浄の少なくとも一方を行うために使用され、有機溶剤を含有するレジスト膜パターニング用の処理液である。本発明の処理液は、SP値が16.3MPa1/2以下の第一の有機溶剤と、SP値が17.1MPa1/2以上の第二の有機溶剤と、を含む。
本発明の処理液によれば、レジストL/Sパターンにおけるパターン倒れの発生とレジストC/Hパターンにおける抜け不良の発生を同時に抑制できる。この理由の詳細は未だ明らかになっていないが、以下のように推測される。
以上の様に、現像液及び/又はリンス液として用いられる上記の処理液は、SP値の異なる少なくとも2種の有機溶剤を含有することで、レジストL/Sパターンにおけるパターン倒れの発生とレジストC/Hパターンにおける抜け不良の発生を同時に抑制できる。
また、特に、より後に行われる工程で用いられる処理液として、SP値が16.3MPa1/2以下の第一の有機溶剤とSP値が17.1MPa1/2以上の第二の有機溶剤とを含む処理液を用いることが好ましく、すなわち、リンス液に本発明の処理液を用いることが好ましい。
以下において、まず有機溶剤について説明し、次いで処理液に含まれる得る酸化防止剤及び界面活性剤について説明する。
SP値が16.3MPa1/2以下の第一の有機溶剤としては種々の有機溶剤から選択されるが、例えば、炭化水素系溶剤、エーテル系溶剤、及びエステル系溶剤等の溶剤を用いることができる。第一の有機溶剤のSP値の下限は、特に限定されないが、例えば14.5MPa1/2以上である。
これらのなかでも、SP値が16.3MPa1/2以下の炭化水素系溶剤、又はエーテル系溶剤が好ましく、SP値が16.3MPa1/2以下の炭化水素系溶剤がより好ましい。
また、第一の有機溶剤のSP値は、16.0MPa1/2以下が好ましく、15.0~16.0MPa1/2の範囲とすることがより好ましい。SP値をこの範囲とすることで、C/Hの抜け不良をも向上させることができる。
レジストL/Sパターンにおけるパターン倒れの発生とレジストC/Hパターンにおける抜け不良の発生を同時に抑制できる効果(以下、「本発明の効果」ともいう)をより一層優れたものとする観点から、上記SP値が16.3MPa1/2以下の第一の有機溶剤は、比誘電率が4.0以下であることが好ましく、3.0以下が好ましく、2.5以下がより好ましい。
なお、「比誘電率」は、「Handbook of Organic Solvent Properties、Ian M. Smallwood著、1996、Elsevier」及び「CRC Handbook of Chemistry and Physics, 96th Edition、William M. Haynes著、2015、CRC Press」に記載の比誘電率(主に温度20℃に於ける値)を用いたものである。
ペンタン(14.5)、ヘキサン(14.9)、ヘプタン(15.2)、オクタン(15.5)、ノナン(15.7)、デカン(15.8)、ウンデカン(16.0)、ドデカン(16.1)、ヘキサデカン(16.2)、2,2,4-トリメチルペンタン(14.3)、2,2,3-トリメチルヘキサン(14.6)、イソヘキサン(14.4)、イソヘプタン(14.8)、イソオクタン(15.1)、イソデカン(15.5)、イソドデカン(14.7)、及びイソヘキサデカン(15.0)等の脂肪族炭化水素系溶剤;、
オクテン(15.6)、ノネン(15.8)、デセン(16.0)、ウンデセン(16.1)、及びドデセン(16.2)等の不飽和炭化水素系溶剤が挙げられる。
不飽和炭化水素溶剤が有する二重結合又は三重結合の数は特に限定されず、また、炭化水素鎖のどの位置に有してもよい(但し、上述の値は、炭素差の1位が二重結合で置換された場合を示した)。また、不飽和炭化水素溶剤が二重結合を有する場合には、cis体及びtrans体が混在していてもよい。
炭化水素系溶剤である脂肪族炭化水素系溶剤においては、SP値が上記範囲内であれば、同じ炭素数で異なる構造の化合物の混合物であってもよい。例えば、脂肪族炭化水素系溶媒としてデカンを使用した場合、同じ炭素数で異なる構造の化合物である2-メチルノナン(15.5)、2,2-ジメチルオクタン(15.2)、及び4-エチルオクタン(15.5)等が脂肪族炭化水素系溶媒に含まれていてもよい。
また、上記同じ炭素数で異なる構造の化合物は、1種のみが含まれていてもよいし、上記のように複数種含まれていてもよい。
なお、上記脂肪族炭化水素系溶剤の炭素数の上限値は特に限定されないが、例えば、16以下が挙げられ、14以下が好ましく、12以下がより好ましい。
上記脂肪族炭化水素系溶剤のなかでも、好ましくは、デカン(15.8)、ウンデカン(16.0)、又はイソデカン(15.5)であり、より好ましくはウンデカン(16.0)である。
例えば、ジペンチルエーテル(16.2)、ジブチルエーテル(15.9)、及びジプロピルエーテル(15.5)等の非環式脂肪族エーテル系溶剤;
ジ-2-エチルヘキシルエーテル(15.9)、ジイソペンチルエーテル(15.6)、ジイソブチルエーテル(15.2)、ジイソプロピルエーテル(14.6)、ジイソヘキシルエーテル(15.6)、エチルイソペンチルエーテル(15.4)、プロピルイソペンチルエーテル(15.6)、メチルイソブチルエーテル(14.7)、エチルイソブチルエーテル(15.1)、プロピルイソブチルエーテル(15.4)、及びエチルイソプロピルエーテル(14.7)等の分岐アルキル基を有する非環式脂肪族エーテル系溶剤が挙げられる。
特に好ましくは、ジイソブチルエーテル(15.2)又はジイソペンチルエーテル(15.6)である。
SP値が17.1MPa1/2以上の第二の有機溶剤としては種々の有機溶剤から選択されるが、例えば、ケトン系溶剤、エステル系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、及び炭化水素系溶剤を用いることができる。第二の有機溶剤のSP値の上限は、特に限定されないが、例えば27.0MPa1/2以下である。
これらのなかでも、SP値が17.1MPa1/2以上のケトン系溶剤、又はエステル系溶剤が好ましく、SP値が17.1MPa1/2以上のケトン系溶剤がより好ましい。
また、第二の有機溶剤のSP値は、17.1~23.0MPa1/2が好ましく、17.1~20.0MPa1/2がより好ましく、17.1~18.1MPa1/2が更に好ましい。SP値をこの範囲とすることで、L/Sのパターン倒れをも向上させることができる。
本発明の効果をより一層優れたものとする観点から、上記SP値が17.1MPa1/2以上の第二の有機溶剤は、比誘電率が6.0以上であることが好ましく、6以上20以下が好ましく、6以上14以下がより好ましく、6以上10以下が更に好ましい。
これらのなかでも、酢酸ブチル(17.8)、酢酸アミル(17.8)、酢酸イソアミル(17.4)、酢酸2-メチルブチル(17.4)、酢酸1-メチルブチル(17.4)、酢酸ヘキシル(17.8)、プロピオン酸ペンチル(17.8)、プロピオン酸ヘキシル(17.7)、プロピオン酸ヘプチル(17.7)、ブタン酸ブチル(17.8)、又は、イソブタン酸イソブチル(17.1)が好ましく、酢酸イソアミル(17.4)がより好ましい。
なかでも、本発明の効果がより優れる観点から、非環状のケトン系溶剤(非環状ケトン)が好ましく、2-オクタノン(18.0)、3-オクタノン(18.0)、4-オクタノン(18.0)、2-ノナノン(18.0)、3-ノナノン(18.0)、4-ノナノン(18.0)、5-ノナノン(18.0)、2-ヘプタノン(18.1)、3-ヘプタノン(18.1)、4-ヘプタノン(18.1)、ジイソブチルケトン(17.4)、ジイソペンチルケトン(17.4)、ジイソヘキシルケトン(17.4)、又はジイソヘプチルケトン(17.4)がより好ましく、ジイソブチルケトン(17.4)、ジイソペンチルケトン(17.4)、ジイソヘキシルケトン(17.4)、ジイソヘプチルケトン(17.4)、4-ヘプタノン(18.1)、又は5-ノナノン(18.0)が更に好ましく、ジイソブチルケトン(17.4)が特に好ましい。
エチレングリコール(36.5)、ジエチレングリコール(30.6)、及びトリエチレングリコール(27.8)等のグリコール系溶剤;、
エチレングリコールモノメチルエーテル(24.5)、プロピレングリコールモノメチルエーテル(PGME;別名1-メトキシ-2-プロパノール)(23.0)、ジエチレングリコールモノメチルエーテル(23.0)、トリエチレングリコールモノエチルエーテル(21.7)、3-メトキシ3-メチルブタノール(21.5)、エチレングリコールモノエチルエーテル(23.5)、エチレングリコールモノプロピルエーテル(22.7)、エチレングリコールモノブチルエーテル(22.1)、プロピレングリコールモノエチルエーテル(22.3)、プロピレングリコールモノプロピルエーテル(21.8)、プロピレングリコールモノブチルエーテル(21.4)、及びプロピレングリコールモノフェニルエーテル(24.2)等の水酸基を含有するグリコールエーテル系溶剤;等を挙げることができる。
これらのなかでもグリコールエーテル系溶剤を用いることが好ましい。
また、第二の有機溶剤の含有量は、処理液の全質量に対して、通常5~95質量%であり、好ましくは10~70質量%であり、更に好ましくは10~60質量%である。
第一の有機溶剤と第二の有機溶剤との質量比(第一の有機溶剤/第二の有機溶剤)は特に制限されないが、0.25~9が好ましく、0.4~3がより好ましい。
イオン性液体としては、例えば、陽イオンとして、ピリジニウムイオン若しくはイミダゾリウムイオン等の芳香族系イオン、又は、トリメチルヘキシルアンモニウムイオン等の脂肪族アミン系イオン等を有し、陰イオンとしてNO3 -、CH3CO2 -、BF6 -、若しくはPF6 -等の無機イオン系、又は、(CF3SO2)2N-、CF3CO2 -、若しくはCF3SO2 -等のフッ素含有有機陰イオン等を有したイオン性液体;4級アンモニウム塩系イオン性液体が好ましく用いられる。
パターン形成において本発明の処理液をリンス液として用いた場合、現像液としては特に限定されず、本発明の処理液、又は、後述する本発明の処理液と併用可能な現像液(特に好ましくはエステル系溶剤)を用いることが好ましい。
また、パターン形成において本発明の処理液を現像液として用いた場合、リンス液としては特に限定されず、本発明の処理液、又は、後述する本発明の処理液と併用可能なリンス液を用いることが好ましい。
また、下記に示す現像液に用いられる有機溶剤、及びリンス液に用いられる有機溶剤は、現像液及びリンス液から選ばれる各液において、それぞれ上述の第一の有機溶剤及び第二の有機溶剤と併用可能な有機溶剤(SP値が上述の範囲を満たさない有機溶剤)でもある。言い換えると、現像液は、上述した述の第一の有機溶剤及び第二の有機溶剤と、下記に示す現像液に用いられる有機溶剤とをいずれも含有する液として調製することができる。また、リンス液は、上述した述の第一の有機溶剤及び第二の有機溶剤と、下記に示すリンス液に用いられる有機溶剤とをいずれも含有する液として調製することができる。なお、以下に説明する有機溶剤中には、SP値が上述した範囲に含まれる有機溶剤(言い換えると、SP値が16.3MPa1/2以下の有機溶剤、又はSP値が17.1MPa1/2以上の有機溶剤)も含まれているが、これらのSP値が上述した範囲に含まれる有機溶剤については、第一の有機溶剤及び第二の有機溶剤のいずれかに該当するものとする。つまり、現像液及びリンス液が、第一の有機溶剤及び第二の有機溶剤のほかに、他の有機溶剤を含有する場合、上記他の有機溶剤は、下記に説明する有機溶剤中のSP値が上述の範囲を満たさない有機溶剤から選ばれる。
現像液に用いられる有機溶剤の蒸気圧(混合溶媒である場合は全体としての蒸気圧)は、20℃に於いて、5kPa以下が好ましく、3kPa以下が更に好ましく、2kPa以下が特に好ましい。有機溶剤の蒸気圧を5kPa以下にすることにより、現像液の基板上又は現像カップ内での蒸発が抑制され、ウエハ面内の温度均一性が向上し、結果としてウエハ面内の寸法均一性が良化する。
現像液に用いられる有機溶剤としては、種々の有機溶剤が広く使用されるが、例えば、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、及び炭化水素系溶剤等の溶剤を用いることができる。
また、炭化水素系溶剤としては、不飽和炭化水素系溶剤も用いることができ、例えば、オクテン、ノネン、デセン、ウンデセン、ドデセン、及びヘキサデセン等の不飽和炭化水素系溶剤が挙げられる。不飽和炭化水素溶剤が有する二重結合又は三重結合の数は特に限定されず、また、炭化水素鎖のどの位置に有してもよい。また、不飽和炭化水素溶剤が二重結合を有する場合には、cis体及びtrans体が混在していてもよい。
なお、炭化水素系溶剤である脂肪族炭化水素系溶剤においては、同じ炭素数で異なる構造の化合物の混合物であってもよい。例えば、脂肪族炭化水素系溶媒としてデカンを使用した場合、同じ炭素数で異なる構造の化合物である2-メチルノナン、2,2-ジメチルオクタン、4-エチルオクタン、及びイソオクタン等が脂肪族炭化水素系溶媒に含まれていてもよい。
また、上記同じ炭素数で異なる構造の化合物は、1種のみが含まれていてもよいし、上記のように複数種含まれていてもよい。
上記エステル系溶剤のヘテロ原子は、炭素原子及び水素原子以外の原子であって、例えば、酸素原子、窒素原子、及び硫黄原子等が挙げられる。ヘテロ原子数は、2以下が好ましい。
炭素数が6以上かつヘテロ原子数が2以下のエステル系溶剤の好ましい例としては、酢酸ブチル、酢酸アミル、酢酸イソアミル、酢酸2-メチルブチル、酢酸1-メチルブチル、酢酸ヘキシル、プロピオン酸ペンチル、プロピオン酸ヘキシル、プロピオン酸ヘプチル、ブタン酸ブチル、及びイソブタン酸ブチルから選ばれる少なくとも1種であることが好ましく、酢酸イソアミル、又はイソブタン酸ブチルが更に好ましい。
エステル系溶剤と炭化水素系溶剤とを組み合わせて用いる場合には、エステル系溶剤として酢酸イソアミルを用いることが好ましい。また、炭化水素系溶剤としては、レジスト膜の溶解性を調製するという観点から、飽和炭化水素溶剤(例えば、オクタン、ノナン、デカン、ドデカン、ウンデカン、及びヘキサデカン等)を用いることが好ましい。
ケトン系溶剤としては、例えば、1-オクタノン、2-オクタノン、1-ノナノン、2-ノナノン、アセトン、2-ヘプタノン(メチルアミルケトン)、4-ヘプタノン、1-ヘキサノン、2-ヘキサノン、ジイソブチルケトン、2,5-ジメチル-4-ヘキサノン、シクロヘキサノン、メチルシクロヘキサノン、フェニルアセトン、メチルエチルケトン、メチルイソブチルケトン、アセチルアセトン、アセトニルアセトン、イオノン、ジアセトニルアルコール、アセチルカービノール、アセトフェノン、メチルナフチルケトン、イソホロン、及びプロピレンカーボネート等を挙げることができ、ジイソブチルケトン、2,5-ジメチル-4-ヘキサノンを用いることが好ましい。
上記の混合溶剤を用いる場合において、炭化水素系溶剤の含有量は、レジスト膜の溶剤溶解性に依存するため、特に限定されず、適宜調製して必要量を決定すればよい。
現像液における有機溶剤(複数混合の場合は合計)の濃度は、好ましくは50質量%以上、より好ましくは85質量%以上、より好ましくは90質量%以上、特に好ましくは95質量%以上であり、最も好ましくは、実質的に有機溶剤のみからなる場合である。なお、実質的に有機溶剤のみからなる場合とは、現像液を100質量%で含有する場合のほか微量の界面活性剤、酸化防止剤、安定剤、及び消泡剤等の成分を含有する場合を含むものとする。
R及びR’についてのアルキル基、アルコキシル基、及びアルコキシカルボニル基の炭素数は、1~15の範囲であることが好ましく、シクロアルキル基の炭素数は、3~15であることが好ましい。
R及びR’としては水素原子又はアルキル基が好ましく、R及びR’についてのアルキル基、シクロアルキル基、アルコキシル基、アルコキシカルボニル基、及びRとR’とが互いに結合して形成する環は、水酸基、カルボニル基を含む基(例えば、アシル基、アルデヒド基、及びアルコキシカルボニル等)、又はシアノ基等で置換されていてもよい。
一般式(S1)で表される溶剤としては、酢酸アルキルであることが好ましく、酢酸ブチル、酢酸アミル(酢酸ペンチル)、又は酢酸イソアミル(酢酸イソペンチル)であることがより好ましく、酢酸イソアミルであることが更に好ましい。
R’’及びR’’’’は、各々独立に、水素原子、アルキル基、シクロアルキル基、アルコキシル基、アルコキシカルボニル基、カルボキシル基、ヒドロキシル基、シアノ基又はハロゲン原子を表す。R’’及びR’’’’は、互いに結合して環を形成してもよい。
R’’及びR’’’’は、水素原子又はアルキル基であることが好ましい。R’’及びR’’’’についてのアルキル基、アルコキシル基、及びアルコキシカルボニル基の炭素数は、1~15の範囲であることが好ましく、シクロアルキル基の炭素数は、3~15であることが好ましい。
R’’’は、アルキレン基又はシクロアルキレン基を表す。R’’’は、アルキレン基であることが好ましい。R’’’についてのアルキレン基の炭素数は、1~10の範囲であることが好ましい。R’’’についてのシクロアルキレン基の炭素数は、3~10の範囲であることが好ましい。
R’’及びR’’’’についてのアルキル基、シクロアルキル基、アルコキシル基、アルコキシカルボニル基、R’’’についてのアルキレン基、シクロアルキレン基、及びR’’とR’’’’とが互いに結合して形成する環は、水酸基、カルボニル基を含む基(例えば、アシル基、アルデヒド基、及びアルコキシカルボニル等)、又はシアノ基等で置換されていてもよい。
これらのなかでも、R’’及びR’’’’が無置換のアルキル基であり、R’’’が無置換のアルキレン基であることが好ましく、R’’及びR’’’’がメチル基及びエチル基のいずれかであることがより好ましく、R’’及びR’’’’がメチル基であることが更により好ましい。
なかでも、下記一般式(S3)で表される溶剤が好ましく、アニソールがより好ましい。
RSは、アルキル基を表す。アルキル基としては炭素数1~4が好ましく、メチル基又はエチル基がより好ましく、メチル基であることが更に好ましい。
リンス液の蒸気圧(混合溶媒である場合は全体としての蒸気圧)は、20℃に於いて0.05kPa以上、5kPa以下が好ましく、0.1kPa以上、5kPa以下がより好ましく、0.12kPa以上、3kPa以下が更に好ましい。リンス液の蒸気圧を0.05kPa以上、5kPa以下にすることにより、ウエハ面内の温度均一性が向上し、更にはリンス液の浸透に起因した膨潤が抑制され、ウエハ面内の寸法均一性が良化する。
これらの有機溶剤の具体例は、上記現像液で説明した有機溶剤と同様である。
なお、上記脂肪族炭化水素系溶剤の炭素数の上限値は特に限定されないが、例えば、16以下が挙げられ、14以下が好ましく、12以下がより好ましい。
上記脂肪族炭化水素系溶剤のなかでも、特に好ましくは、デカン、ウンデカン、又はドデカンであり、最も好ましくはウンデカンである。
なお、リンス液に含まれる炭化水素系溶剤として不飽和炭化水素系溶剤も用いることができ、例えば、オクテン、ノネン、デセン、ウンデセン、ドデセン、及びヘキサデセン等の不飽和炭化水素系溶剤が挙げられる。不飽和炭化水素溶剤が有する二重結合又は三重結合の数は特に限定されず、また、炭化水素鎖のどの位置に有してもよい。また、不飽和炭化水素溶剤が二重結合を有する場合には、cis体及びtrans体が混在していてもよい。
このようにリンス液に含まれる有機溶剤として炭化水素系溶剤(特に脂肪族炭化水素系溶剤)を用いることで、現像後にわずかにレジスト膜に染み込んでいた現像液が洗い流されて、膨潤がより抑制され、パターン倒れが抑制されるという効果が一層発揮される。
リンス液が、エステル系溶剤及びケトン系溶剤からなる群より選択される少なくとも1種を含有する場合、酢酸ブチル、酢酸イソペンチル(酢酸イソアミル)、酢酸n-ペンチル、3-エトキシプロピオン酸エチル(EEP、エチル-3-エトキシプロピオネート)、及び2-ヘプタノンからなる群より選択される少なくとも1種の溶剤を主成分として含有することが好ましく、酢酸ブチル及び2-ヘプタノンからなる群より選択される少なくとも1種の溶剤を主成分として含有することが特に好ましい。
また、リンス液が、エステル系溶剤及びケトン系溶剤からなる群より選択される少なくとも1種を含有する場合、エステル系溶剤、グリコールエーテル系溶剤、ケトン系溶剤、及びアルコール系溶剤からなる群より選択される溶剤を副成分として含有することが好ましく、なかでも、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、プロピレングリコールモノメチルエーテル(PGME)、酢酸エチル、乳酸エチル、3-メトキシプロピオン酸メチル、シクロヘキサノン、メチルエチルケトン、γ-ブチロラクトン、プロパノール、3-メトキシ-1-ブタノール、N-メチルピロリドン、及びプロピレンカーボネートからなる群より選択される溶剤が好ましい。
このなかでも、有機溶剤としてエステル系溶剤を用いる場合には、上記効果が一層発揮されるという点から、2種以上のエステル系溶剤を用いることが好ましい。この場合の具体例としては、エステル系溶剤(好ましくは酢酸ブチル)を主成分として、これとは化学構造が異なるエステル系溶剤(好ましくは、プロピレングリコールモノメチルエーテルアセテート(PGMEA))を副成分として用いることが挙げられる。
また、有機溶剤としてエステル系溶剤を用いる場合には、上記効果が一層発揮されるという点から、エステル系溶剤(1種又は2種以上)に加えて、グリコールエーテル系溶剤を用いてもよい。この場合の具体例としては、エステル系溶剤(好ましくは、酢酸ブチル)を主成分として、グリコールエーテル系溶剤(好ましくはプロピレングリコールモノメチルエーテル(PGME))を副成分として用いることが挙げられる。
有機溶剤としてケトン系溶剤を用いる場合には、上記効果が一層発揮されるという点から、ケトン系溶剤(1種又は2種以上)に加えて、エステル系溶剤及び/又はグリコールエーテル系溶剤を用いてもよい。この場合の具体例としては、ケトン系溶剤(好ましくは2-ヘプタノン)を主成分として、エステル系溶剤(好ましくは、プロピレングリコールモノメチルエーテルアセテート(PGMEA))及び/又はグリコールエーテル系溶剤(好ましくは、プロピレングリコールモノメチルエーテル(PGME))を副成分として用いることが挙げられる。
ここで、上記の「主成分」とは、有機溶剤の全質量に対する含有量が、50~100質量%であることをいい、好ましくは70~100質量%、より好ましくは80~100質量%、更に好ましくは90~100質量%、特に好ましくは95~100質量%であることをいう。
また、副成分を含有する場合には、副成分の含有量は、主成分の全質量(100質量%)に対して、0.1~20質量%であることが好ましく、0.5~10質量%であることがより好ましく、1~5質量%であることが更に好ましい。
<界面活性剤>
処理液は、界面活性剤を含有することが好ましい。これにより、レジスト膜に対する濡れ性が向上して、現像及び/又はリンスがより効果的に進行する。
界面活性剤としては、後述する感活性光線又は感放射線性組成物に用いられる界面活性剤と同様のものを用いることができる。
界面活性剤の含有量は、処理液の全質量に対して、通常0.001~5質量%、好ましくは0.005~2質量%、より好ましくは0.01~0.5質量%である。
処理液は、酸化防止剤を含有することが好ましい。これにより、経時的な酸化剤の発生を抑制でき、酸化剤の含有量をより低下できる。
アミン系酸化防止剤としては、例えば、1-ナフチルアミン、フェニル-1-ナフチルアミン、p-オクチルフェニル-1-ナフチルアミン、p-ノニルフェニル-1-ナフチルアミン、p-ドデシルフェニル-1-ナフチルアミン、及びフェニル-2-ナフチルアミン等のナフチルアミン系酸化防止剤;N,N'-ジイソプロピル-p-フェニレンジアミン、N,N'-ジイソブチル-p-フェニレンジアミン、N,N'-ジフェニル-p-フェニレンジアミン、N,N'-ジ-β-ナフチル-p-フェニレンジアミン、N-フェニル-N'-イソプロピル-p-フェニレンジアミン、N-シクロヘキシル-N'-フェニル-p-フェニレンジアミン、N-1,3-ジメチルブチル-N'-フェニル-p-フェニレンジアミン、ジオクチル-p-フェニレンジアミン、フェニルヘキシル-p-フェニレンジアミン、及びフェニルオクチル-p-フェニレンジアミン等のフェニレンジアミン系酸化防止剤;ジピリジルアミン、ジフェニルアミン、p,p'-ジ-n-ブチルジフェニルアミン、p,p'-ジ-t-ブチルジフェニルアミン、p,p'-ジ-t-ペンチルジフェニルアミン、p,p'-ジオクチルジフェニルアミン、p,p'-ジノニルジフェニルアミン、p,p'-ジデシルジフェニルアミン、p,p'-ジドデシルジフェニルアミン、p,p'-ジスチリルジフェニルアミン、p,p'-ジメトキシジフェニルアミン、4,4'-ビス(4-α,α-ジメチルベンゾイル)ジフェニルアミン、p-イソプロポキシジフェニルアミン、及びジピリジルアミン等のジフェニルアミン系酸化防止剤;フェノチアジン、N-メチルフェノチアジン、N-エチルフェノチアジン、3,7-ジオクチルフェノチアジン、フェノチアジンカルボン酸エステル、及びフェノセレナジン等のフェノチアジン系酸化防止剤が挙げられる。
フェノール系酸化防止剤としては、例えば、2,6-ジ-ターシャリブチルフェノール(以下、ターシャリブチルをt-ブチルと略記する。)、2,6-ジ-t-ブチル-p-クレゾール、2,6-ジ-t-ブチル-4-メチルフェノール、2,6-ジ-t-ブチル-4-エチルフェノール、2,4-ジメチル-6-t-ブチルフェノール、4,4’-メチレンビス(2,6-ジ-t-ブチルフェノール)、4,4’-ビス(2,6-ジ-t-ブチルフェノール)、4,4’-ビス(2-メチル-6-t-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、2,2’-メチレンビス(4-エチル-6-t-ブチルフェノール)、4,4’-ブチリデンビス(3-メチル-6-t-ブチルフェノール)、4,4’-イソプロピリデンビス(2,6-ジ-t-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-シクロヘキシルフェノール)、2,2’-メチレンビス(4-メチル-6-ノニルフェノール)、2,2’-イソブチリデンビス(4,6-ジメチルフェノール)、2,6-ビス(2’-ヒドロキシ-3’-t-ブチル-5’-メチルベンジル)-4-メチルフェノール、3-t-ブチル-4-ヒドロキシアニソール、2-t-ブチル-4-ヒドロキシアニソール、3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオン酸オクチル、3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオン酸ステアリル、3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオン酸オレイル、3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオン酸ドデシル、3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオン酸デシル、3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオン酸オクチル、テトラキス{3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオニルオキシメチル}メタン、3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオン酸グリセリンモノエステル、3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオン酸とグリセリンモノオレイルエーテルとのエステル、3-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)プロピオン酸ブチレングリコールジエステル、2,6-ジ-t-ブチル-α-ジメチルアミノ-p-クレゾール、2,6-ジ-t-ブチル-4-(N,N’-ジメチルアミノメチルフェノール)、トリス{(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオニル―オキシエチル}イソシアヌレート、トリス(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)イソシアヌレート、1,3,5-トリス(3,5-ジ-t-ブチル-4-ヒドロキシベンジル)イソシアヌレート、1,3,5-トリス(4-t-ブチル-3-ヒドロキシ-2,6―ジメチルベンジル)イソシアヌレート、N,N’-ヘキサメチレンビス(3,5-ジ-t-ブチル-4-ヒドロキシ-ヒドロシナミド)、3,9-ビス〔1,1-ジメチル-2-{β-(3-t-ブチル-4-ヒドロキシ-5-メチルフェニル)プロピオニルオキシ}エチル〕-2,4,8,10-テトラオキサスピロ[5,5]ウンデカン、1,1,3-トリス(2-メチル-4-ヒドロキシ-5-t-ブチルフェニル)ブタン、1,3,5-トリメチル-2,4,6-トリス(3,5-ジ-t-ブチル-4-ヒドロキシベンジル)ベンゼン、及び、ビス{3,3’-ビス-(4’-ヒドロキシ-3’-t-ブチルフェニル)ブチリックアシッド}グリコールエステル等が挙げられる。
本発明の処理液は、塩基性化合物を含有することが好ましい。塩基性化合物の具体例としては、後に述べる感活性光線性又は感放射線性組成物が含み得る塩基性化合物(E)として例示する化合物が挙げられる。
本発明の処理液に含まれ得る塩基性化合物のなかでも、以下の含窒素化合物を好ましく用いることができる。
上記含窒素化合物が現像液に含まれる場合、含窒素化合物は、酸の作用によりレジスト膜中に発生する極性基と相互作用し、有機溶剤に対する露光部の不溶性を更に向上させることができる。ここで、上記含窒素化合物と極性基との相互作用とは、この含窒素化合物と極性基が反応して塩を形成する作用、及びイオン性結合を形成する作用等を意味する。
SP値(Fedors法)=[(各置換基の凝集エネルギーの和)/(各置換基の体積の和)]0.5
なお、本発明において、上記の含窒素化合物は、1種のみを使用してもよいし、化学構造が異なる2種以上を併用してもよい。
非化学増幅系のレジストとしては、例えば、下記のものが挙げられる。
(1)g線、h線、i線、KrF、ArF、EBあるいはEUV等の照射によって主鎖が切断し、分子量が低下することにより溶解性が変化するレジスト材料(例えば特開2013-210411号公報の段落0025~0029、0056、及び、米国特許公報2015/0008211の段落0032~0036、0063に記載のα-クロロアクリル酸エステル系化合物とα-メチルスチレン系化合物との共重合体を主成分とするレジスト材料等)
(2)g線、h線、i線、KrF、ArF、EBあるいはEUV等によって生じたシラノール縮合反応を伴うハイドロゲンシルセスオキサン(HSQ)、塩素置換したカリックスアレーン等のレジスト材料
(3)g線、h線、i線、KrF、ArF、EBあるいはEUV等の光に対して吸収を有する金属錯体(マグネシウム、クロム、マンガン、鉄、コバルト、ニッケル、銅、亜鉛、銀、カドミウム、インジウム、錫、アンチモン、セシウム、ジルコニウム、ハフニウム等の錯体であり、チタン、ジルコニウム、ハフニウムがパターン形成性の観点から好ましい)を含み、配位子脱離及び/又は光酸発生剤と併用して配位子交換過程を伴うレジスト(特開2015-075500号公報の段落0017~0033、0037~0047、特開2012-185485号公報の段落0017~0032、0043~0044、米国特許公報2012/0208125の段落0042~0051、0066等に記載のレジスト材料)等。
シリコン系のレジストとしては、例えば、特開2008-83384号公報に記載の段落0010~0062、段落0129~0165に記載のレジスト材料が挙げられる。
本発明のパターン形成方法は、感活性光線又は感放射線性組成物(以下「レジスト組成物」ともいう)を用いてレジスト膜を形成するレジスト膜形成工程と、上記レジスト膜を露光する露光工程と、露光された上記レジスト膜を上述した処理液によって処理する処理工程と、を含む。
本発明のパターン形成方法によれば、上述した処理液を用いるので、レジストL/Sパターンにおけるパターン倒れの発生とレジストC/Hパターンにおける抜け不良の発生を同時に抑制できる。
レジスト膜形成工程は、感活性光線性又は感放射線性組成物を用いてレジスト膜を形成する工程であり、例えば次の方法により行うことができる。
感活性光線性又は感放射線性組成物を用いて基板上にレジスト膜(感活性光線性又は感放射線性組成物膜)を形成するためには、後述する各成分を溶剤に溶解して感活性光線性又は感放射線性組成物を調製し、必要に応じてフィルター濾過した後、基板上に塗布する。フィルターとしては、好ましくはポアサイズ0.1ミクロン以下、より好ましくは0.05ミクロン以下、更に好ましくは0.03ミクロン以下のポリテトラフロロエチレン製、ポリエチレン製、又はナイロン製のものが好ましい。
加熱温度は、80~180℃で行うことが好ましく、80~150℃で行うことがより好ましく、80~140℃で行うことが更に好ましく、80~130℃で行うことが特に好ましい。
加熱時間は、30~1000秒が好ましく、60~800秒がより好ましく、60~600秒が更に好ましい。
例えば30nm以下のサイズの1:1ラインアンドスペースパターンを解像させるためには、形成されるレジスト膜の膜厚が50nm以下であることが好ましい。膜厚が50nm以下であれば、後述する現像工程を適用した際に、パターン倒れがより起こりにくくなり、より優れた解像性能が得られる。
膜厚の範囲としてより好ましくは、15nm~45nmの範囲である。膜厚が15nm以上であれば、十分なエッチング耐性が得られる。膜厚の範囲として更に好ましくは、15nm~40nmである。膜厚がこの範囲にあると、エッチング耐性とより優れた解像性能とを同時に満足させることができる。
露光工程は、上記レジスト膜を露光する工程であり、例えば次の方法により行うことができる。
上記のようにして形成したレジスト膜に、所定のマスクを通して活性光線又は放射線を照射する。なお、電子ビームの照射では、マスクを介さない描画(直描)が一般的である。なお、製膜後、露光工程の前に、露光前ベーク工程(塗布後ベーク工程ともいう(PB;Prebake))を含むことも好ましい。
活性光線又は放射線としては特に限定されないが、例えばKrFエキシマレーザー、ArFエキシマレーザー、EUV光(Extreme Ultra Violet)、及び電子線(EB、Electron Beam)等である。露光は液浸露光であってもよい。
本発明のパターン形成方法においては、露光工程の後かつ現像工程の前に、露光後ベーク工程(PEB;Post Exposure Bake)を含むことも好ましい。露光後ベーク工程により露光部の反応が促進され、感度又はパターン形状がより良好となる。
加熱温度は、80~150℃が好ましく、80~140℃がより好ましく、80~130℃が更に好ましい。
加熱時間は、30~1000秒が好ましく、60~800秒がより好ましく、60~600秒が更に好ましい。
加熱は通常の露光・現像機に備わっている手段で行うことができ、ホットプレート等を用いて行ってもよい。
なお、上述した露光前ベーク工程の加熱温度及び加熱時間についても、上述の露光後ベーク工程の加熱温度及び加熱時間と同様である。
現像工程は、露光された上記レジスト膜を現像液によって現像する工程である。
また、現像を行う工程の後に、他の溶媒に置換しながら、現像を停止する工程を実施してもよい。
現像時間は未露光部の樹脂が十分に溶解する時間であれば特に制限はなく、通常は10~300秒であり、好ましくは20~120秒である。
現像液の温度は、0~50℃が好ましく、15~35℃がより好ましい。
リンス工程は、上記現像工程の後にリンス液によって洗浄(リンス)する工程である。
洗浄処理の方法は特に限定されないが、例えば、一定速度で回転している基板上にリンス液を吐出しつづける方法(回転吐出法)、リンス液が満たされた槽中に基板を一定時間浸漬する方法(ディップ法)、及び、基板表面にリンス液を噴霧する方法(スプレー法)等を適用することができ、このなかでも回転吐出方法で洗浄処理を行い、洗浄後に基板を2000rpm~4000rpmの回転数で回転させ、リンス液を基板上から除去することが好ましい。
リンス時間には特に制限はないが、通常は10秒~300秒であり。好ましくは10秒~180秒であり、最も好ましくは20秒~120秒である。
リンス液の温度は、0~50℃が好ましく、15~35℃が更に好ましい。
さらに、現像処理又はリンス処理又は超臨界流体による処理の後、パターン中に残存する溶剤を除去するために加熱処理を行うことができる。加熱温度は、良好なレジストパターンが得られる限り特に限定されるものではなく、通常40~160℃である。加熱温度は50~150℃が好ましく、50~110℃が最も好ましい。加熱時間に関しては良好なレジストパターンが得られる限り特に限定されないが、通常15~300秒であり、好ましくは、15~180秒である。
上記問題を解決するためには、再度、レジストが溶解する溶剤を配管に通す方法がある。配管に通す方法としては、リンス液での洗浄後に基板の背面及び側面等をレジストが溶解する溶剤で洗浄して流す方法、又は、レジストに接触させずにレジストが溶剤する溶剤を配管を通るように流す方法が挙げられる。
配管に通す溶剤としては、レジストを溶解し得るものであれば特に限定されず、例えば上述した現像液として用いられる溶剤が挙げられる。具体的には、プロピレングリコールモノメチルエーテルアセテート(PGMEA)、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテルプロピオネート、プロピレングリコールモノエチルエーテルプロピオネート、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテル(PGME)、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、2-ヘプタノン、乳酸エチル、1-プロパノール、及びアセトン等が挙げられる。なかでも、PGMEA、PGME、又はシクロヘキサノンが好ましい。
次に、本発明の処理液を組み合わせて用いることが好ましい感活性光線性又は感放射線性組成物について詳細に説明する。以下、まず、感活性光線性又は感放射線性組成物が含み得る成分について説明する。
本発明の処理液と組み合わせて用いることが好ましい感活性光線性又は感放射線性組成物としては、「樹脂(A))」を含有することが好ましい。樹脂(A)は、少なくとも(i)酸の作用により分解してカルボキシル基を生じる基を有する繰り返し単位(更に、フェノール性水酸基を有する繰り返し単位を有してもよい)、又は、少なくとも(ii)フェノール系水酸基を有する繰り返し単位を有する。
なお、酸の作用により分解してカルボキシル基を有する繰り返し単位を有すると、酸の作用によりアルカリ現像液に対する溶解度が増大し、有機溶剤に対する溶解度が減少する。
R41、R42及びR43は、各々独立に、水素原子、アルキル基、ハロゲン原子、シアノ基又はアルコキシカルボニル基を表す。但し、R42はAr4と結合して環を形成していてもよく、その場合のR42は単結合又はアルキレン基を表す。
X4は、単結合、-COO-、又は-CONR64-を表し、R64は、水素原子又はアルキル基を表す。
L4は、単結合又はアルキレン基を表す。
Ar4は、(n+1)価の芳香環基を表し、R42と結合して環を形成する場合には(n+2)価の芳香環基を表す。
nは、1~5の整数を表す。
一般式(I)におけるR41、R42、及びR43のハロゲン原子としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられ、フッ素原子が好ましい。
一般式(I)におけるR41、R42、及びR43のアルコキシカルボニル基に含まれるアルキル基としては、上記R41、R42、及びR43におけるアルキル基と同様のものが好ましい。
(n+1)価の芳香環基は、更に置換基を有していてもよい。
X4により表わされる-CONR64-(R64は、水素原子、又はアルキル基を表す)におけるR64のアルキル基としては、置換基を有していてもよいメチル基、エチル基、プロピル基、イソプロピル基、n-ブチル基、sec-ブチル基、ヘキシル基、2-エチルヘキシル基、オクチル基、及びドデシル基等の炭素数20以下のアルキル基が好ましく、炭素数8以下のアルキル基がより好ましい。
X4としては、単結合、-COO-、又は-CONH-が好ましく、単結合、又は-COO-がより好ましい。
Ar4としては、置換基を有していてもよい炭素数6~18の芳香環基がより好ましく、ベンゼン環基、ナフタレン環基、又はビフェニレン環基が特に好ましい。
一般式(I)で表される繰り返し単位は、ヒドロキシスチレン構造を備えていることが好ましい。即ち、Ar4は、ベンゼン環基であることが好ましい。
式中、R36~R39は、各々独立に、アルキル基、シクロアルキル基、アリール基、アラルキル基又はアルケニル基を表す。R36とR37とは、互いに結合して環を形成してもよい。
R01及びR02は、各々独立に、水素原子、アルキル基、シクロアルキル基、アリール基、アラルキル基、又はアルケニル基を表す。
Xa1は、水素原子、又は置換基を有していてもよいアルキル基を表す。
Tは、単結合、又は2価の連結基を表す。
Rx1~Rx3は、各々独立に、アルキル基(直鎖若しくは分岐)、又はシクロアルキル基(単環若しくは多環)を表す。ただし、Rx1~Rx3の全てがアルキル基(直鎖若しくは分岐)である場合、Rx1~Rx3のうち少なくとも2つはメチル基であることが好ましい。
Rx1~Rx3の2つが結合して、シクロアルキル基(単環若しくは多環)を形成してもよい。
Tの2価の連結基としては、アルキレン基、-COO-Rt-基、及び-O-Rt-基等が挙げられる。式中、Rtは、アルキレン基又はシクロアルキレン基を表す。
Tは、単結合又は-COO-Rt-基が好ましい。Rtは、炭素数1~5のアルキレン基が好ましく、-CH2-基、-(CH2)2-基、又は-(CH2)3-基がより好ましい。
Rx1~Rx3のシクロアルキル基としては、シクロペンチル基、及びシクロヘキシル基等の単環のシクロアルキル基、ノルボルニル基、テトラシクロデカニル基、テトラシクロドデカニル基、及びアダマンチル基等の多環のシクロアルキル基が好ましい。
Rx1~Rx3の2つが結合して形成されるシクロアルキル基としては、シクロペンチル基、及びシクロヘキシル基等の単環のシクロアルキル基、ノルボルニル基、テトラシクロデカニル基、テトラシクロドデカニル基、及びアダマンチル基等の多環のシクロアルキル基が好ましい。炭素数5~6の単環のシクロアルキル基がより好ましい。
Rx1~Rx3の2つが結合して形成されるシクロアルキル基は、例えば、環を構成するメチレン基の1つが、酸素原子等のヘテロ原子、又は、カルボニル基等のヘテロ原子を有する基で置き換わっていてもよい。
一般式(AI)で表される繰り返し単位は、例えば、Rx1がメチル基又はエチル基であり、Rx2とRx3とが結合して上述のシクロアルキル基を形成している態様が好ましい。
具体例中、Rx、及びXa1は、水素原子、CH3、CF3、又はCH2OHを表す。Rxa、及びRxbは各々炭素数1~4のアルキル基を表す。Zは、極性基を含む置換基を表し、複数存在する場合は各々独立である。pは0又は正の整数を表す。Zにより表される極性基を含む置換基としては、例えば、水酸基、シアノ基、アミノ基、アルキルアミド基又はスルホンアミド基を有する直鎖、分岐又は環状のアルキル基が挙げられ、好ましくは、水酸基を有するアルキル基である。分岐状アルキル基としてはイソプロピル基が特に好ましい。
ラクトン基としては、ラクトン構造を含有していればいずれの基でもよいが、5~7員環ラクトン構造を含有する基が好ましく、5~7員環ラクトン構造にビシクロ構造又はスピロ構造を形成する形で他の環構造が縮環しているものがより好ましい。
ラクトン基を有する繰り返し単位としては、下記一般式(LC1-1)~(LC1-16)のいずれかで表されるラクトン構造を有する基を含有する繰り返し単位を有することが好ましい。好ましいラクトン構造としては一般式(LC1-1)、(LC1-4)、(LC1-5)、(LC1-6)、(LC1-13)、又は(LC1-14)で表される基である。また、ラクトン構造を有する基が主鎖に直接結合していてもよい。
Rb0のアルキル基が有していてもよい好ましい置換基としては、水酸基、及びハロゲン原子が挙げられる。
Rb0のハロゲン原子としては、フッ素原子、塩素原子、臭素原子、及び沃素原子を挙げることができる。Rb0は、水素原子又はメチル基が好ましい。
Abは、単結合、アルキレン基、単環又は多環の脂環炭化水素構造を有する2価の連結基、エーテル基、エステル基、カルボニル基、カルボキシル基、又はこれらを組み合わせた2価の基を表す。好ましくは、単結合、又は-Ab1-CO2-で表される連結基である。Ab1は、直鎖若しくは分岐アルキレン基、又は、単環若しくは多環のシクロアルキレン基であり、好ましくは、メチレン基、エチレン基、シクロヘキシレン基、アダマンチレン基、又は、ノルボルニレン基である。
Vは、一般式(LC1-1)~(LC1-16)のうちのいずれかで示される基を表す。
樹脂(A)は、極性基を有する有機基を含有する繰り返し単位、特に、極性基で置換された脂環炭化水素構造を有する繰り返し単位を更に有することができる。
これにより基板密着性、及び/又は現像液親和性が向上する。極性基で置換された脂環炭化水素構造の脂環炭化水素構造としてはアダマンチル基、ジアマンチル基、又はノルボルナン基が好ましい。極性基としては水酸基、又はシアノ基が好ましい。
極性基を有する繰り返し単位の具体例を以下に挙げるが、本発明はこれらに限定されない。
このような繰り返し単位としては、例えば、下記一般式(4)で表される繰り返し単位が挙げられる。
反応溶媒としては、例えば、テトラヒドロフラン、1,4-ジオキサン、及びジイソプロピルエーテル等のエーテル類;メチルエチルケトン、及びメチルイソブチルケトン等のケトン類;酢酸エチル等のエステル溶媒;ジメチルホルムアミド、及びジメチルアセトアミド等のアミド溶剤;後述のプロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテル、及びシクロヘキサノン等の感活性光線性又は感放射線性組成物を溶解する溶媒;等が挙げられる。より好ましくは感活性光線性又は感放射線性組成物に用いられる溶剤と同一の溶剤を用いて重合することが好ましい。これにより保存時のパーティクルの発生が抑制できる。
反応温度は、通常10℃~150℃であり、好ましくは30℃~120℃、更に好ましくは60~100℃である。
精製は、水洗又は適切な溶媒を組み合わせることにより残留単量体及びオリゴマー成分を除去する液液抽出法、特定の分子量以下のもののみを抽出除去する限外ろ過等の溶液状態での精製方法、樹脂溶液を貧溶媒へ滴下することで樹脂を貧溶媒中に凝固させることにより残留単量体等を除去する再沈殿法、及び、濾別した樹脂スラリーを貧溶媒で洗浄する等の固体状態での精製方法等の通常の方法を適用できる。
樹脂(A)の重量平均分子量の特に好ましい別の形態は、GPC法によるポリスチレン換算値で3,000~9,500である。重量平均分子量を3,000~9,500にすることにより、特にレジスト残渣(以降、「スカム」ともいう)が抑制され、より良好なパターンを形成することができる。
分散度(分子量分布)は、通常1~5であり、好ましくは1~3、更に好ましくは1.2~3.0、特に好ましくは1.2~2.0の範囲のものが使用される。分散度の小さいものほど、解像度及びレジスト形状が優れ、且つレジストパターンの側壁がスムーズであり、ラフネス性に優れる。
また、感活性光線性又は感放射線性組成物において、樹脂(A)は、1種で使用してもよいし、複数併用してもよい。
R61、R62及びR63は、各々独立に、水素原子、アルキル基、シクロアルキル基、ハロゲン原子、シアノ基、又はアルコキシカルボニル基を表す。但し、R62はAr6と結合して環を形成していてもよく、その場合のR62は単結合又はアルキレン基を表す。
X6は、単結合、-COO-、又は-CONR64-を表す。R64は、水素原子又はアルキル基を表す。
L6は、単結合又はアルキレン基を表す。
Ar6は、(n+1)価の芳香環基を表し、R62と結合して環を形成する場合には(n+2)価の芳香環基を表す。
Y2は、n≧2の場合には、各々独立に、水素原子又は酸の作用により脱離する基を表す。但し、Y2の少なくとも1つは、酸の作用により脱離する基を表す。
nは、1~4の整数を表す。
酸の作用により脱離する基Y2としては、下記一般式(VI-A)で表される構造がより好ましい。
Mは、単結合又は2価の連結基を表す。
Qは、アルキル基、ヘテロ原子を含んでいてもよいシクロアルキル基、ヘテロ原子を含んでいてもよいアリール基、アミノ基、アンモニウム基、メルカプト基、シアノ基又はアルデヒド基を表す。
Q、M、L1の少なくとも2つが結合して環(好ましくは、5員若しくは6員環)を形成してもよい。
Ar3は、芳香環基を表す。
R3は、水素原子、アルキル基、シクロアルキル基、アリール基、アラルキル基、アルコキシ基、アシル基又はヘテロ環基を表す。
M3は、単結合又は2価の連結基を表す。
Q3は、アルキル基、シクロアルキル基、アリール基又はヘテロ環基を表す。
Q3、M3及びR3の少なくとも二つが結合して環を形成してもよい。
R41、R42及びR43は、各々独立に、水素原子、アルキル基、シクロアルキル基、ハロゲン原子、シアノ基又はアルコキシカルボニル基を表す。R42はL4と結合して環を形成していてもよく、その場合のR42はアルキレン基を表す。
L4は、単結合又は2価の連結基を表し、R42と環を形成する場合には3価の連結基を表す。
R44及びR45は、水素原子、アルキル基、シクロアルキル基、アリール基、アラルキル基、アルコキシ基、アシル基又はヘテロ環基を表す。
M4は、単結合又は2価の連結基を表す。
Q4は、アルキル基、シクロアルキル基、アリール基又はヘテロ環基を表す。
Q4、M4及びR44の少なくとも二つが結合して環を形成してもよい。
R41、R42及びR43は、前述の一般式(V)中のR51、R52、及びR53と同義であり、また好ましい範囲も同様である。
L4は、前述の一般式(V)中のL5と同義であり、また好ましい範囲も同様である。
R44及びR45は、前述の一般式(3)中のR3と同義であり、また好ましい範囲も同様である。
M4は、前述の一般式(3)中のM3と同義であり、また好ましい範囲も同様である。
Q4は、前述の一般式(3)中のQ3と同義であり、また好ましい範囲も同様である。
Q4、M4及びR44の少なくとも二つが結合して形成される環としては、Q3、M3及びR3の少なくとも二つが結合して形成される環があげられ、また好ましい範囲も同様である。
以下に一般式(4)で表される繰り返し単位の具体例を示すが、本発明はこれに限定されるものではない。
R1は、水素原子、アルキル基、シクロアルキル基、ハロゲン原子、シアノ基又はアルキルオキシカルボニル基を表す。
R6及びR7は、それぞれ独立に、水素原子、ヒドロキシ基、炭素数1~10の直鎖状、分岐状若しく環状のアルキル基、アルコキシ基又はアシロキシ基、シアノ基、ニトロ基、アミノ基、ハロゲン原子、エステル基(-OCOR又は-COOR:Rは炭素数1~6のアルキル基又はフッ素化アルキル基)、又はカルボキシル基を表す。
n3は0~6の整数を表す。
n4は0~4の整数を表す。
X4はメチレン基、酸素原子又は硫黄原子である
一般式(V)又は一般式(VI)で表される繰り返し単位の具体例を下記に示すが、これらに限定されない。
シルセスキオキサン構造としては、例えば、カゴ型シルセスキオキサン構造、はしご型シルセスキオキサン構造(ラダー型シルセスキオキサン構造)、及びランダム型シルセスキオキサン構造等が挙げられる。なかでも、カゴ型シルセスキオキサン構造が好ましい。
ここで、カゴ型シルセスキオキサン構造とは、カゴ状骨格を有するシルセスキオキサン構造である。カゴ型シルセスキオキサン構造は、完全カゴ型シルセスキオキサン構造であっても、不完全カゴ型シルセスキオキサン構造であってもよいが、完全カゴ型シルセスキオキサン構造であることが好ましい。
又はしご型シルセスキオキサン構造とは、はしご状骨格を有するシルセスキオキサン構造である。
また、ランダム型シルセスキオキサン構造とは、骨格がランダムのシルセスキオキサン構造である。
上記有機基は特に制限されないが、具体例としては、ヒドロキシ基、ニトロ基、カルボキシ基、アルコキシ基、アミノ基、メルカプト基、ブロック化メルカプト基(例えば、アシル基でブロック(保護)されたメルカプト基)、アシル基、イミド基、ホスフィノ基、ホスフィニル基、シリル基、ビニル基、ヘテロ原子を有していてもよい炭化水素基、(メタ)アクリル基含有基及びエポキシ基含有基等が挙げられる。
上記ヘテロ原子を有していてもよい炭化水素基のヘテロ原子としては、例えば、酸素原子、窒素原子、硫黄原子、及びリン原子等が挙げられる。
上記ヘテロ原子を有していてもよい炭化水素基の炭化水素基としては、例えば、脂肪族炭化水素基、芳香族炭化水素基、又はこれらを組み合わせた基等が挙げられる。
上記脂肪族炭化水素基は、直鎖状、分岐鎖状、及び環状のいずれであってもよい。上記脂肪族炭化水素基の具体例としては、直鎖状又は分岐状のアルキル基(特に、炭素数1~30)、直鎖状又は分岐状のアルケニル基(特に、炭素数2~30)、及び直鎖状又は分岐状のアルキニル基(特に、炭素数2~30)等が挙げられる。
上記芳香族炭化水素基としては、例えば、フェニル基、トリル基、キシリル基、及びナフチル基等の炭素数6~18の芳香族炭化水素基等が挙げられる。
感活性光線性又は感放射線性樹脂組成物は、活性光線又は放射線により酸を発生する化合物(以下、「光酸発生剤《PAG:Photo Acid Generator》」ともいう)を含有することが好ましい。
光酸発生剤は、低分子化合物の形態であってもよく、重合体の一部に組み込まれた形態であってもよい。また、低分子化合物の形態と重合体の一部に組み込まれた形態を併用してもよい。
光酸発生剤が、低分子化合物の形態である場合、分子量が3000以下であることが好ましく、2000以下であることがより好ましく、1000以下であることが更に好ましい。
光酸発生剤が、重合体の一部に組み込まれた形態である場合、樹脂(A)の一部に組み込まれてもよく、樹脂(A)とは異なる樹脂に組み込まれてもよい。
本発明において、光酸発生剤が、低分子化合物の形態であることが好ましい。
光酸発生剤としては、公知のものであれば特に限定されないが、活性光線又は放射線、好ましくは電子線又は極紫外線の照射により、有機酸、例えば、スルホン酸、ビス(アルキルスルホニル)イミド、又はトリス(アルキルスルホニル)メチドの少なくともいずれかを発生する化合物が好ましい。
より好ましくは下記一般式(ZI)、(ZII)、又は(ZIII)で表される化合物を挙げることができる。
R201、R202及びR203は、各々独立に、有機基を表す。
R201、R202及びR203としての有機基の炭素数は、一般的に1~30、好ましくは1~20である。
また、R201~R203のうち2つが結合して環構造を形成してもよく、環内に酸素原子、硫黄原子、エステル結合、アミド結合、又はカルボニル基を含んでいてもよい。R201~R203の内の2つが結合して形成する基としては、アルキレン基(例えば、ブチレン基、ペンチレン基)を挙げることができる。
Z-は、非求核性アニオン(求核反応を起こす能力が著しく低いアニオン)を表す。
各基が有するアリール基及び環構造については、置換基として更にアルキル基(好ましくは炭素数1~15)を挙げることができる。
また、ビス(アルキルスルホニル)イミドアニオンにおけるアルキル基は、互いに結合して環構造を形成してもよい。これにより、酸強度が増加する。
Xfは、それぞれ独立に、フッ素原子、又は少なくとも1つのフッ素原子で置換されたアルキル基を表す。
R1、及びR2は、それぞれ独立に、水素原子、フッ素原子、又は、アルキル基を表し、複数存在する場合のR1、及びR2は、それぞれ同一でも異なっていてもよい。
Lは、二価の連結基を表し、複数存在する場合のLは同一でも異なっていてもよい。
Aは、環状の有機基を表す。
xは1~20の整数を表し、yは0~10の整数を表し、zは0~10の整数を表す。
Xfのフッ素原子で置換されたアルキル基におけるアルキル基としては、好ましくは炭素数1~10であり、より好ましくは炭素数1~4である。また、Xfのフッ素原子で置換されたアルキル基は、パーフルオロアルキル基であることが好ましい。
Xfとして好ましくは、フッ素原子又は炭素数1~4のパーフルオロアルキル基である。Xfの具体的としては、フッ素原子、CF3、C2F5、C3F7、C4F9、CH2CF3、CH2CH2CF3、CH2C2F5、CH2CH2C2F5、CH2C3F7、CH2CH2C3F7、CH2C4F9、及びCH2CH2C4F9が挙げられ、なかでもフッ素原子、CF3が好ましい。
特に、双方のXfがフッ素原子であることが好ましい。
R1、及びR2としては、好ましくはフッ素原子又はCF3である。
yは0~4が好ましく、0がより好ましい。
zは0~5が好ましく、0~3がより好ましい。
Lの2価の連結基としては特に限定されず、―COO-、-OCO-、-CO-、-O-、-S―、-SO―、―SO2-、アルキレン基、シクロアルキレン基、アルケニレン基、及びこれらの複数が連結した連結基等を挙げることができ、総炭素数12以下の連結基が好ましい。このなかでも―COO-、-OCO-、-CO-、又は-O-が好ましく、―COO-、又は-OCO-がより好ましい。
脂環基としては、単環でも多環でもよく、シクロペンチル基、シクロヘキシル基、及び、シクロオクチル基等の単環のシクロアルキル基;ノルボルニル基、トリシクロデカニル基、テトラシクロデカニル基、テトラシクロドデカニル基、及び、アダマンチル基等の多環のシクロアルキル基が好ましい。なかでも、ノルボルニル基、トリシクロデカニル基、テトラシクロデカニル基、テトラシクロドデカニル基、及びアダマンチル基等の炭素数7以上のかさ高い構造を有する脂環基が、露光後加熱工程での膜中拡散性を抑制でき、MEEF(mask error enhancement factor)向上の観点から好ましい。
アリール基としては、ベンゼン環、ナフタレン環、フェナンスレン環、及びアントラセン環が挙げられる。
複素環基としては、フラン環、チオフェン環、ベンゾフラン環、ベンゾチオフェン環、ジベンゾフラン環、ジベンゾチオフェン環、及びピリジン環由来のものが挙げられる。なかでもフラン環、チオフェン環、又はピリジン環由来のものが好ましい。
なお、上記置換基は、上記(LC1-1)~(LC1-17)においてはRb2に相当する。また、上記(LC1-1)~(LC1-17)において、n2は0~4の整数を表す。n2が2以上の時、複数存在するRb2は、同一でも異なっていてもよく、また、複数存在するRb2同士が結合して環を形成してもよい。
R201、R202及びR203のうち、少なくとも1つがアリール基であることが好ましく、三つ全てがアリール基であることがより好ましい。アリール基としては、フェニル基、及びナフチル基等の他に、インドール残基、及びピロール残基等のヘテロアリール基も可能である。R201~R203のアルキル基及びシクロアルキル基としては、好ましくは、炭素数1~10の直鎖又は分岐アルキル基、及び炭素数3~10のシクロアルキル基を挙げることができる。アルキル基としては、メチル基、エチル基、n-プロピル基、i-プロピル基、又は、n-ブチル基等が好ましい。シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、又は、シクロへプチル基が好ましい。これらの基は更に置換基を有していてもよい。その置換基としては、ニトロ基、フッ素原子等のハロゲン原子、カルボキシル基、水酸基、アミノ基、シアノ基、アルコキシ基(好ましくは炭素数1~15)、シクロアルキル基(好ましくは炭素数3~15)、アリール基(好ましくは炭素数6~14)、アルコキシカルボニル基(好ましくは炭素数2~7)、アシル基(好ましくは炭素数2~12)、及びアルコキシカルボニルオキシ基(好ましくは炭素数2~7)等が挙げられるが、これらに限定されるものではない。
一般式(ZII)、及び(ZIII)中、R204~R207は、各々独立に、アリール基、アルキル基又はシクロアルキル基を表す。
R204~R207のアリール基としてはフェニル基、又はナフチル基が好ましく、更に好ましくはフェニル基である。R204~R207のアリール基は、酸素原子、窒素原子、又は硫黄原子等を有する複素環構造を有するアリール基であってもよい。複素環構造を有するアリール基の骨格としては、例えば、ピロール、フラン、チオフェン、インドール、ベンゾフラン、及びベンゾチオフェン等を挙げることができる。
R204~R207におけるアルキル基及びシクロアルキル基としては、炭素数1~10の直鎖若しく分岐アルキル基(例えば、メチル基、エチル基、プロピル基、ブチル基、及びペンチル基)、又は、炭素数3~10のシクロアルキル基(シクロペンチル基、シクロヘキシル基、及びノルボニル基)が好ましい。
本発明においては、活性光線又は放射線の照射により以下に例示する酸を発生する光酸発生剤が好ましい。なお、例の一部には、体積の計算値を付記している(単位Å3)。なお、ここで求めた計算値は、アニオン部にプロトンが結合した酸の体積値である。
光酸発生剤の感活性光線性又は感放射線性樹脂組成物中の含有量は、組成物の全固形分を基準として、0.1~50質量%が好ましく、より好ましくは5~50質量%、更に好ましくは8~40質量%である。特に、電子線又は極紫外線露光の際に高感度化、高解像性を両立するには光酸発生剤の含有率は高い方が好ましく、より好ましくは10~40質量%、更に好ましくは10~35質量%である。
上述した各成分を溶解させて感活性光線性又は感放射線性樹脂組成物を調製する際には、溶剤を使用できる。使用できる溶剤としては、例えば、アルキレングリコールモノアルキルエーテルカルボキシレート、アルキレングリコールモノアルキルエーテル、乳酸アルキルエステル、アルコキシプロピオン酸アルキル、炭素数4~10の環状ラクトン、炭素数4~10の、環を含有してもよいモノケトン化合物、アルキレンカーボネート、アルコキシ酢酸アルキル、及び、ピルビン酸アルキル等の有機溶剤を挙げることができる。
アルキレングリコールモノアルキルエーテルとしては、例えば、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、エチレングリコールモノメチルエーテル、又はエチレングリコールモノエチルエーテルが好ましい。
アルコキシプロピオン酸アルキルとしては、例えば、3-エトキシプロピオン酸エチル、3-メトキシプロピオン酸メチル、3-エトキシプロピオン酸メチル、又は3-メトキシプロピオン酸エチルが好ましい。
アルコキシ酢酸アルキルとしては、例えば、酢酸-2-メトキシエチル、酢酸-2-エトキシエチル、酢酸-2-(2-エトキシエトキシ)エチル、酢酸-3-メトキシ-3-メチルブチル、酢酸-1-メトキシ-2-プロピルが好ましく挙げられる。
ピルビン酸アルキルとしては、例えば、ピルビン酸メチル、ピルビン酸エチル、又はピルビン酸プロピルが好ましい。
好ましく使用できる溶剤としては、常温常圧下で、沸点130℃以上の溶剤が挙げられる。具体的には、シクロペンタノン、γ-ブチロラクトン、シクロヘキサノン、乳酸エチル、エチレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、3-エトキシプロピオン酸エチル、ピルビン酸エチル、酢酸-2-エトキシエチル、酢酸-2-(2-エトキシエトキシ)エチル、及びプロピレンカーボネートが挙げられる。
本発明に於いては、上記溶剤を単独で使用してもよいし、2種類以上を併用してもよい。
水酸基を含有する溶剤としては、例えば、エチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、及び乳酸エチル等を挙げることができ、これらのなかでも、プロピレングリコールモノメチルエーテル、又は乳酸エチルが好ましい。
水酸基を含有しない溶剤としては、例えば、プロピレングリコールモノメチルエーテルアセテート、エチルエトキシプロピオネート、2-ヘプタノン、γ-ブチロラクトン、シクロヘキサノン、酢酸ブチル、N-メチルピロリドン、N,N-ジメチルアセトアミド、及びジメチルスルホキシド等を挙げることができ、これらのなかでも、プロピレングリコールモノメチルエーテルアセテート、エチルエトキシプロピオネート、2-ヘプタノン、γ-ブチロラクトン、シクロヘキサノン、又は酢酸ブチルが好ましく、プロピレングリコールモノメチルエーテルアセテート、エチルエトキシプロピオネート、又は2-ヘプタノンがより好ましい。
水酸基を含有する溶剤と水酸基を含有しない溶剤との混合比(質量)は、好ましくは1/99~99/1、より好ましくは10/90~90/10、更に好ましくは20/80~60/40である。水酸基を含有しない溶剤を50質量%以上含有する混合溶剤が塗布均一性の点で特に好ましい。
感活性光線性又は感放射線性樹脂組成物は、露光から加熱までの経時による性能変化を低減するために、(E)塩基性化合物を含有することが好ましい。
塩基性化合物としては、好ましくは、下記式(A)~(E)で示される構造を有する化合物を挙げることができる。
R203、R204、R205及びR206は、同一でも異なってもよく、炭素数1~20個のアルキル基を表す。
これら一般式(A)及び(E)中のアルキル基は、無置換であることがより好ましい。
また、アミン化合物は、アルキル鎖中に、酸素原子を有し、オキシアルキレン基が形成されていることが好ましい。オキシアルキレン基の数は、分子内に1つ以上、好ましくは3~9個、より好ましくは4~6個である。オキシアルキレン基のなかでもオキシエチレン基(-CH2CH2O-)若しくオキシプロピレン基(-CH(CH3)CH2O-若しくは-CH2CH2CH2O-)が好ましく、より好ましくはオキシエチレン基である。
アンモニウム塩化合物は、アルキル鎖中に、酸素原子を有し、オキシアルキレン基が形成されていることが好ましい。オキシアルキレン基の数は、分子内に1つ以上、好ましくは3~9個、より好ましくは4~6個である。オキシアルキレン基のなかでもオキシエチレン基(-CH2CH2O-)若しくはオキシプロピレン基(-CH(CH3)CH2O-若しくは-CH2CH2CH2O-)が好ましく、より好ましくはオキシエチレン基である。
アンモニウム塩化合物のアニオンとしては、ハロゲン原子、スルホネート、ボレート、及びフォスフェート等が挙げられるが、なかでもハロゲン原子、又はスルホネートが好ましい。ハロゲン原子としてはクロライド、ブロマイド、又はアイオダイドが好ましく、スルホネートとしては、炭素数1~20の有機スルホネートが好ましい。有機スルホネートとしては、炭素数1~20のアルキルスルホネート、及びアリールスルホネートが挙げられる。アルキルスルホネートのアルキル基は置換基を有していてもよく、置換基としては例えばフッ素、塩素、臭素、アルコキシ基、アシル基、及びアリール基等が挙げられる。アルキルスルホネートとして、具体的にはメタンスルホネート、エタンスルホネート、ブタンスルホネート、ヘキサンスルホネート、オクタンスルホネート、ベンジルスルホネート、トリフルオロメタンスルホネート、ペンタフルオロエタンスルホネート、及びノナフルオロブタンスルホネート等が挙げられる。アリールスルホネートのアリール基としてはベンゼン環、ナフタレン環、及びアントラセン環が挙げられる。ベンゼン環、ナフタレン環、及びアントラセン環は置換基を有していてもよく、置換基としては炭素数1~6の直鎖若しくは分岐アルキル基、又は、炭素数3~6のシクロアルキル基が好ましい。直鎖若しくは分岐アルキル基、及びシクロアルキル基としては、具体的には、メチル、エチル、n-プロピル、イソプロピル、n-ブチル、i-ブチル、t-ブチル、n-ヘキシル、及びシクロヘキシル等が挙げられる。他の置換基としては炭素数1~6のアルコキシ基、ハロゲン原子、シアノ、ニトロ、アシル基、及びアシルオキシ基等が挙げられる。
本発明に係る組成物は、塩基性化合物として、プロトンアクセプター性官能基を有し、かつ、活性光線又は放射線の照射により分解してプロトンアクセプター性が低下、消失、又はプロトンアクセプター性から酸性に変化した化合物を発生する化合物〔以下、化合物(PA)ともいう〕を更に含んでいてもよい。
感活性光線性又は感放射線性樹脂組成物は、上記樹脂(A)とは別に疎水性樹脂(A’)を有していてもよい。
疎水性樹脂はレジスト膜の表面に偏在するように設計されることが好ましいが、界面活性剤とは異なり、必ずしも分子内に親水基を有する必要はなく、極性/非極性物質を均一に混合することに寄与しなくてもよい。
疎水性樹脂を添加することの効果として、水に対するレジスト膜表面の静的/動的な接触角の制御、アウトガスの抑制等を挙げることができる。
フッ素原子を有するアルキル基(好ましくは炭素数1~10、より好ましくは炭素数1~4)は、少なくとも1つの水素原子がフッ素原子で置換された直鎖又は分岐アルキル基であり、更にフッ素原子以外の置換基を有していてもよい。
フッ素原子を有するシクロアルキル基は、少なくとも1つの水素原子がフッ素原子で置換された単環又は多環のシクロアルキル基であり、更にフッ素原子以外の置換基を有していてもよい。
フッ素原子を有するアリール基としては、フェニル基、及びナフチル基等のアリール基の少なくとも1つの水素原子がフッ素原子で置換されたものが挙げられ、更にフッ素原子以外の置換基を有していてもよい。
フッ素原子又は珪素原子を有する繰り返し単位の例としては、US2012/0251948A1の段落0519に例示されたものを挙げることが出来る。
ここで、疎水性樹脂中の側鎖部分が有するCH3部分構造には、エチル基、及びプロピル基等が有するCH3部分構造を包含するものである。
一方、疎水性樹脂の主鎖に直接結合しているメチル基(例えば、メタクリル酸構造を有する繰り返し単位のα-メチル基)は、主鎖の影響により疎水性樹脂の表面偏在化への寄与が小さいため、本発明におけるCH3部分構造に包含されないものとする。
感活性光線性又は感放射線性樹脂組成物は、界面活性剤(F)を更に含んでいてもよい。界面活性剤を含有することにより、波長が250nm以下、特には220nm以下の露光光源を使用した場合に、良好な感度及び解像度で、密着性及び現像欠陥のより少ないパターンを形成することが可能となる。
界面活性剤としては、フッ素系及び/又はシリコン系界面活性剤を用いることが特に好ましい。
フッ素系及び/又はシリコン系界面活性剤としては、例えば、米国特許出願公開第2008/0248425号明細書の[0276]に記載の界面活性剤が挙げられる。また、エフトップEF301若しくはEF303(新秋田化成(株)製);フロラードFC430、431若しくは4430(住友スリーエム(株)製);メガファックF171、F173、F176、F189、F113、F110、F177、F120若しくはR08(DIC(株)製);サーフロンS-382、SC101、102、103、104、105若しくは106(旭硝子(株)製);トロイゾルS-366(トロイケミカル(株)製);GF-300若しくはGF-150(東亜合成化学(株)製)、サーフロンS-393(セイミケミカル(株)製);エフトップEF121、EF122A、EF122B、RF122C、EF125M、EF135M、EF351、EF352、EF801、EF802若しくはEF601((株)ジェムコ製);PF636、PF656、PF6320若しくはPF6520(OMNOVA社製);又は、FTX-204G、208G、218G、230G、204D、208D、212D、218D若しくは222D((株)ネオス製)を用いてもよい。なお、ポリシロキサンポリマーKP-341(信越化学工業(株)製)も、シリコン系界面活性剤として用いることができる。
また、米国特許出願公開第2008/0248425号明細書の[0280]に記載されているフッ素系及び/又はシリコン系以外の界面活性剤を使用してもよい。
感活性光線性又は感放射線性樹脂組成物は、溶解阻止化合物、染料、可塑剤、光増感剤、光吸収剤、及び/又は現像液に対する溶解性を促進させる化合物(例えば、分子量1000以下のフェノール化合物、及びカルボキシ基を含んだ脂環族若しくは脂肪族化合物等)を更に含んでいてもよい。
ここで「溶解阻止化合物」とは、酸の作用により分解して有機系現像液中での溶解度が減少する、分子量3000以下の化合物である。
本発明のパターン形成方法においては、レジスト膜の上層に上層膜(トップコート膜)を形成してもよい。
上層膜は、レジスト膜と混合せず、更にレジスト膜上層に均一に塗布できることが好ましい。
上層膜については、特に限定されず、従来公知の上層膜を、従来公知の方法によって形成でき、例えば、特開2014-059543号公報の段落0072~0082の記載に基づいて上層膜を形成できる。上層膜の形成材料は、特開2014-059543号公報の段落0072に記載されるポリマーの他に、疎水性樹脂等も用いることができる。疎水性樹脂は、例えば、上述した疎水性樹脂(A’)を用いることができる。
現像工程において、有機溶剤を含有する現像液を使用する場合は、例えば、特開2013-61648号公報に記載されたような塩基性化合物を含有する上層膜をレジスト膜上に形成することが好ましい。上層膜が含み得る塩基性化合物の具体的な例は、上述した塩基性化合物(E)が挙げられる。
また、上層膜は、エーテル結合、チオエーテル結合、ヒドロキシル基、チオール基、カルボニル結合及びエステル結合からなる群より選択される基又は結合を少なくとも一つ含む化合物を含むことが好ましい。
更に、上層膜は、光酸発生剤を含んでいてもよい。光酸発生剤としては、感活性光線性又は感放射線性組成物に含まれ得る光酸発生剤(例えば、上述した光酸発生剤(B))と同様のものを使用することができる。
以下、上層膜(トップコート膜)に使用されることが好ましい樹脂について説明する。
上層膜形成用組成物は樹脂を含有することが好ましい。上層膜形成用組成物が含有することができる樹脂としては、特に限定されないが、感活性光線性又は感放射線性組成物に含まれ得る疎水性樹脂(例えば、上述した疎水性樹脂(A’))と同様のものを使用することができる。
疎水性樹脂に関しては、特開2013-61647号公報の[0017]~[0023](対応する米国公開特許公報2013/244438号の[0017]~[0023])、及び特開2014-56194号公報の[0016]~[0165]の記載を参酌でき、これらの内容は本願明細書に組み込まれる。
本発明において、上層膜形成用組成物は、芳香環を有する繰り返し単位を含有する樹脂を含むことが好ましい。芳香環を有する繰り返し単位を含有することで、特に電子線又はEUV露光の際に、二次電子の発生効率、及び活性光線又は放射線により酸を発生する化合物からの酸発生効率が高くなり、パターン形成時に高感度化、高解像化の効果が期待できる
樹脂(XA)に含有されるフッ素原子及び珪素原子の含有量の好ましい範囲は、フッ素原子及び/又はケイ素原子を含む繰り返し単位が、樹脂(XA)中10~100質量%であることが好ましく、10~99モル%であることがより好ましく、20~80モル%であることが更に好ましい。
上層膜形成用組成物は、各成分を溶剤に溶解し、フィルター濾過することが好ましい。フィルターとしては、ポアサイズ0.1μm以下、より好ましくは0.05μm以下、更に好ましくは0.03μm以下のポリテトラフロロエチレン製、ポリエチレン製、又はナイロン製のものが好ましい。なお、フィルターは、複数種類を直列又は並列に接続して用いてもよい。また、組成物を複数回濾過してもよく、複数回濾過する工程が循環濾過工程であってもよい。さらに、フィルター濾過の前後で、組成物に対して脱気処理等を行ってもよい。上層膜形成用組成物は、金属等の不純物を含まないことが好ましい。これら材料に含まれる金属成分の含有量としては、10ppm以下が好ましく、5ppm以下がより好ましく、1ppm以下が更に好ましく、実質的に含まないこと(測定装置の検出限界以下であること)が特に好ましい。
なお、上層膜形成用組成物を、感活性光線性又は感放射線性膜の表面に、感活性光線性又は感放射線性膜を溶解せずに均一に塗布するために、上層膜形成用組成物は、感活性光線性又は感放射線性膜を溶解しない溶剤を含有することが好ましい。感活性光線性又は感放射線性膜を溶解しない溶剤としては、有機溶剤を含有する現像液(有機系現像液)とは異なる成分の溶剤を用いることが更に好ましい。
上層膜を形成後、必要に応じて基板を加熱(PB;PreBake)する。
上層膜の屈折率は、解像性の観点から、感活性光線性又は感放射線性膜の屈折率に近いことが好ましい。
上層膜は液浸液に不溶であることが好ましく、水に不溶であることがより好ましい。
上層膜の後退接触角は、液浸液追随性の観点から、上層膜に対する液浸液の後退接触角(23℃)が50~100°であることが好ましく、80~100°であることがより好ましい。
液浸露光においては、露光ヘッドが高速でウエハ上をスキャンし露光パターンを形成していく動きに追随して、液浸液がウエハ上を動く必要があることから、動的な状態における感活性光線性又は感放射線性膜に対する液浸液の接触角が重要になり、より良好なレジスト性能を得るためには、上記範囲の後退接触角を有することが好ましい。
ここで、上層膜の有機系現像液に対する溶解速度とは、上層膜を成膜した後に現像液に暴露した際の膜厚減少速度であり、本発明においては23℃の酢酸ブチルに浸漬させた際の速度とする。
上層膜の有機系現像液に対する溶解速度を1/sec秒以上、好ましくは10nm/sec以上とすることによって、感活性光線性又は感放射線性膜を現像した後の現像欠陥発生が低減する効果がある。また、300nm/sec以下、好ましくは100nm/secとすることによって、おそらくは、液浸露光時の露光ムラが低減した影響で、感活性光線性又は感放射線性膜を現像した後のパターンのラインエッジラフネスがより良好になるという効果がある。
上層膜はその他の公知の現像液、例えば、アルカリ水溶液等を用いて除去してもよい。使用できるアルカリ水溶液として具体的には、テトラメチルアンモニウムヒドロキシドの水溶液が挙げられる。
感活性光線性又は感放射線性樹脂組成物、及び、本発明のパターン形成方法において使用される各種材料(例えば、本発明の処理液(例えば、現像液、又は、リンス液)、レジスト溶剤、反射防止膜形成用組成物、及び上層膜形成用組成物等)は、金属、ハロゲンを含む金属塩、酸、アルカリ、硫黄含有化合物、及びリン含有化合物等の不純物を含まないことが好ましい。これら材料に含まれる不純物の含有量としては、1ppm以下が好ましく、1ppb以下がより好ましく、100ppt以下が更に好ましく、10ppt以下が特に好ましく、実質的に含まないこと(測定装置の検出限界以下であること)が最も好ましい。
上記各種材料から金属等の不純物を除去する方法としては、例えば、フィルターを用いた濾過を挙げることができる。フィルター孔径としては、ポアサイズ10nm以下が好ましく、5nm以下がより好ましく、3nm以下が更に好ましい。フィルターの材質としては、ポリテトラフロロエチレン製、ポリエチレン製、又はナイロン製のフィルターが好ましい。フィルターは、これらの材質とイオン交換メディアを組み合わせた複合材料であってもよい。フィルターは、有機溶剤であらかじめ洗浄したものを用いてもよい。フィルター濾過工程では、複数種類のフィルターを直列又は並列に接続して用いてもよい。複数種類のフィルターを使用する場合は、孔径及び/又は材質が異なるフィルターを組み合わせて使用してもよい。また、各種材料を複数回濾過してもよく、複数回濾過する工程が循環濾過工程であってもよい。
また、上記各種材料に含まれる金属等の不純物を低減する方法としては、各種材料を構成する原料として金属含有量が少ない原料を選択する、各種材料を構成する原料に対してフィルター濾過を行う、及び、装置内をテフロン(登録商標)でライニングする等してコンタミネーションを可能な限り抑制した条件下で蒸留を行う等の方法を挙げることができる。各種材料を構成する原料に対して行うフィルター濾過における好ましい条件は、上記した条件と同様である。
フィルター濾過の他、吸着材による不純物の除去を行ってもよく、フィルター濾過と吸着材を組み合わせて使用してもよい。吸着材としては、公知の吸着材を用いることができ、例えば、シリカゲル、及び、ゼオライト等の無機系吸着材、並びに、活性炭等の有機系吸着材を使用することができる。
現像液及びリンス液等の本発明の処理液としては、収容部を有する、化学増幅型レジスト膜のパターニング用処理液の収容容器に保存されたものを使用することが好ましい。この収容容器としては、例えば、収容部の、処理液に接触する内壁が、ポリエチレン樹脂、ポリプロピレン樹脂、及び、ポリエチレン-ポリプロピレン樹脂のいずれとも異なる樹脂、又は、防錆若しくは金属溶出防止処理が施された金属から形成された、化学増幅型レジスト膜のパターニング用処理液の収容容器であることが好ましい。この収容容器の上記収容部に、化学増幅型レジスト膜のパターニング用処理液として使用される予定の有機溶剤を収容し、化学増幅型レジスト膜のパターニング時において、上記収容部から排出したものを使用することができる。
・Entegris社製 FluoroPurePFA複合ドラム(接液内面;PFA樹脂ライニング)
・JFE社製 鋼製ドラム缶(接液内面;燐酸亜鉛皮膜)
なお、本発明の処理液は、SP値が17.1MPa1/2以上の高極性の有機溶媒を含有するため、それ自体でも静電気の帯電を抑制する効果があるが、上述の導電性の化合物との併用によってより一層、静電気の帯電を抑制することができる。
導電性の化合物としては特に制限されないが、例えば、メタノールが挙げられる。添加量は特に制限されないが、好ましい現像特性を維持する観点で、10質量%以下が好ましく、更に好ましくは、5質量%以下である。薬液配管の部材に関しては、SUS、又は、帯電防止処理の施されたポリエチレン、ポリプロピレン、若しくはフッ素樹脂(ポリテトラフルオロエチレン、及びパーフロオロアルコキシ樹脂等)で被膜された各種配管を用いることができる。フィルター及びO-リングに関しても同様に、帯電防止処理の施されたポリエチレン、ポリプロピレン、又はフッ素樹脂(ポリテトラフルオロエチレン、パーフロオロアルコキシ樹脂等)を用いることができる。
なお、後段の現像又はリンスで使用される処理液(第8表に記載の処理液)に対して、アルカリ、又はハロゲンを含む金属塩の定量分析を行った所、実質的にアルカリ、又はハロゲンを含む金属塩が含まれないことが確認できた。
また、同様に、後段の現像又はリンスで使用される処理液(第8表に記載の処理液)に対して、硫黄含有化合物の定量分析(例えば、JIS K2541-6:2013「硫黄分試験方法(紫外蛍光法)」に規定された方法により測定)及びリン化合物の定量分析(JIS K0102:2013に規定された方法に基づき、全リンとして、吸光光度法により測定)を行ったところ、これらの化合物が実質的に含まれないことが確認できた。
なお、ここで、「実質的に含有しない」とは、これらの化合物の含有量(濃度)を測定可能な方法で測定した場合において、検出されないこと(検出限界値未満であること)をいう。
以下、実施例及び比較例の処理方法の処理対象となるレジスト組成物及び上層膜形成用組成物に用いられる各種成分と、それらの調製方法とについて説明する。
<樹脂(A)等>
(合成例1)樹脂(A-1)の合成
2Lフラスコにシクロヘキサノン600gを入れ、100mL/minの流量で一時間窒素置換した。その後、重合開始剤V-601(和光純薬工業(株)製)4.60g(0.02mol)を加え、内温が80℃になるまで昇温した。次に、以下のモノマーと重合開始剤V-601(和光純薬工業(株)製)4.60g(0.02mol)とを、シクロヘキサノン200gに溶解し、モノマー溶液を調製した。モノマー溶液を上記80℃に加熱したフラスコ中に6時間かけて滴下した。滴下終了後、得られた溶液を、更に80℃で2時間反応させた。
4-アセトキシスチレン 48.66g(0.3mol)
1-エチルシクロペンチルメタクリレート 109.4g(0.6mol)
モノマー1 22.2g(0.1mol)
第3表において、樹脂の組成比(モル比)は、1H-NMR(核磁気共鳴)測定により算出した。樹脂の重量平均分子量(Mw:ポリスチレン換算)、及び分散度(Mw/Mn)はGPC(溶媒:THF)測定により算出した。なお、実施例中に示す他の樹脂についても同様の方法により、重量平均分子量、及び分散度を測定した。
疎水性樹脂としては、以下のものを用いた。
光酸発生剤としては、以下のものを用いた。
塩基性化合物としては、以下のものを用いた。
レジスト溶剤としては、以下のものを用いた。
C-1:プロピレングリコールモノメチルエーテルアセテート
C-2:プロピレングリコールモノメチルエーテル
C-3:乳酸エチル
C-4:シクロヘキサノン
C-5:アニソール
下記第5表に示す各成分を、同表に示す溶剤に溶解させた。これを0.03μmのポアサイズを有するポリエチレンフィルターを用いてろ過して、レジスト組成物を得た。
下記第6表に示す各成分を、同表に示す溶剤に溶解させた。これを0.03μmのポアサイズを有するポリエチレンフィルターを用いてろ過して、上層膜形成用組成物を得た。なお、下記表において「MIBC」はメチルイソブチルカルビノールを表す。
樹脂V-1~V-4、及び1bの組成比、重量平均分子量、並びに分散度については別表(第7表)に示す。
<EUV露光評価>
第5表に記載のレジスト組成物を用いて、以下の操作によりレジストパターンを形成した。
〔レジスト組成物の塗布及び塗布後ベーク(PB)〕
12インチシリコンウエハ(1インチ=2.54cm)上に有機膜DUV44(Brewer Science社製)を塗布し、200℃で60秒間ベークして、膜厚60nmの有機膜を形成した。その上に上記のようにして得られた各レジスト組成物を塗布し、90~180℃の条件(第9表中のPB欄参照)で60秒間ベークし、膜厚40nmのレジスト膜を形成した。
なお、実施例1-24で使用するレジスト組成物31は、ポジ型のレジスト組成物であり、それ以外の実施例及び比較例ではネガ型のレジスト組成物を用いた。
実施例1-30~1-37、及び1-42~1-44については、上記第6表に示す上層膜形成用組成物(トップコート組成物)を上記ベーク後のレジスト膜上に塗布し、その後、下記第9表に示すPB温度(単位:℃)で60秒間に亘ってベークを行い、膜厚40nmの上層膜(トップコート)を形成した。
(L/Sパターン)
上記で作製したウエハに、NA(レンズ開口数、Numerical Aperture)0.25、ダイポール照明(Dipole 60x、アウターシグマ0.81、インナーシグマ0.43)でEUV露光を行った。具体的には、ウエハ上寸法がピッチ40nm、幅20nmのラインアンドスペースパターンを形成する為のパターン(L/Sのパターン倒れ評価用)が含まれたマスクを介して、露光量を変えてEUV露光を行った。
上記で作製したウエハに、NA(レンズ開口数、Numerical Aperture)0.25、Quasar照明(Quasar45、アウターシグマ0.81、インナーシグマ0.51)でEUV露光を行った。具体的には、ウエハ上寸法がピッチ60nm、ホールサイズ30nmのコンタクトホールパターンを形成する為のパターン(C/Hのパターン倒れ評価用)が含まれたマスクを介して、露光量を変えてEUV露光を行った。
照射後、EUV露光装置から取り出したら、ただちに、85~130℃の条件(第9表中のPEB欄参照)で60秒間ベークした。
その後、シャワー型現像装置(ACTES(株)製ADE3000S)を用いて、50回転(rpm)でウエハを回転しながら、現像液(23℃)を、200mL/分の流量で30秒間スプレー吐出することで、現像を行った。なお、現像液としては、第8表に記載のS-1~S-20、及びSA-1~SA-9のいずれかの処理液を用いた。第9表に、各実施例及び比較例で用いた現像液の種類を示す。
また、「比誘電率」は、「Handbook of Organic Solvent Properties、Ian M. Smallwood著、1996、Elsevier」及び「CRC Handbook of Chemistry and Physics, 96th Edition、William M. Haynes著、2015、CRC Press」に記載の比誘電率(主に温度20℃に於ける値)を用いたものである。
その後、50回転(rpm)でウエハを回転しながら、リンス液(23℃)を、200mL/分の流量で15秒間スプレー吐出することで、リンス処理を行った。
最後に、2500回転(rpm)で60秒間高速回転してウエハを乾燥させた。なお、リンス液としては、第8表に記載のS-1~S-20、及びSA-1~SA-9のいずれかの処理液を用いた。第9表に、各実施例及び比較例で用いたリンス液の種類を示す。
以下の項目について、レジストパターンの評価を行った。結果の詳細は第9表に示す。
異なる露光量にて露光したラインアンドスペースパターンの解像状況を、走査型電子顕微鏡((株)日立製作所製S-9380II)を用いて倍率200kで観察し、観察した一視野内にてパターン倒れが起こっていない最小のライン幅を求め、パターン倒れの指標とした。この数値が小さいほど、パターン倒れ性能が良好であることを示す。
異なる露光量にて露光したコンタクトホールパターンの解像状況を、走査型電子顕微鏡((株)日立製作所製S-9380II)を用いて倍率200kで観察し、観察した一視野内にてホールの抜け不良が起こっていない最小のホールサイズを求め、C/Hの抜け性能の指標とした。この数値が小さいほど、C/Hの抜け性能が良好であることを示す。
〔レジスト組成物の塗布及び塗布後ベーク(PB)〕
12インチシリコンウエハ上に有機膜DUV44(Brewer Science社製)を塗布し、200℃で60秒間ベークして、膜厚60nmの有機膜を形成した。その上にレジスト組成物1を塗布し、90℃で60秒間ベークし、膜厚60nmのレジスト膜を形成した。
(L/Sパターン)
上記で作製したウエハに、NA(レンズ開口数、Numerical Aperture)0.25、ダイポール照明(Dipole 60x、アウターシグマ0.81、インナーシグマ0.43)でEUV露光を行った。具体的には、40nmスペース120nmラインパターンのマスクを介して第一のEUV露光を行い、更に、第一のマスクと同じパターンで、マスクの位置を第一の露光スペースとスペースの中間にスペースが配置されるように、80nmずらして第二の露光を行った。
上記で作製したウエハに、NA(レンズ開口数、Numerical Aperture)0.25、ダイポール照明(X偏向、Dipole 60x、アウターシグマ0.81、インナーシグマ0.43)でハーフピッチ30nmラインスペースのマスクを用いて第一のEUV露光を行った。その後、ダイポール照明(Y偏向、Dipole 60y、アウターシグマ0.81、インナーシグマ0.43)でハーフピッチ30nmラインスペースのマスクを用いて第二のEUV露光を行った。
シャワー型現像装置(ACTES(株)製ADE3000S)を用いて、50回転(rpm)でウエハを回転しながら、第8表に示す処理液SA-7を現像液として用いて(23℃)、200mL/分の流量で、30秒間スプレー吐出して現像を行った。
その後、50回転(rpm)でウエハを回転しながら第8表に示す処理液S―11をリンス液として用いて(23℃)、200mL/分の流量で、15秒間スプレー吐出してリンス処理を行った。最後に、2500回転(rpm)で60秒間高速回転してウエハを乾燥させた。
(L/Sパターン評価結果)
パターン形成の為の露光量を適宜調整して露光を行った結果、14nmライン、ピッチ40nmが、パターン倒れなく、解像した。
パターン形成の為の露光量を適宜調整して露光を行った結果、23nmホール、ピッチ60nmが、C/Hの抜け不良なく、解像した。
<EB露光評価>
上記第5表に記載のレジスト組成物を用いて、以下の操作によりレジストパターンを形成した。
6インチシリコンウエハ上に有機膜DUV44(Brewer Science社製)を塗布し、200℃で60秒間ベークして、膜厚60nmの有機膜を形成した。その上に第5表に記載のレジスト組成物を塗布し、90~180℃の条件(第10表中のPB欄参照)で60秒間ベークし、膜厚40nmのレジスト膜を形成した。
なお、実施例2-24で使用するレジスト組成物31はポジ型のレジスト組成物であり、それ以外の実施例及び比較例ではネガ型のレジスト組成物を用いた。
(L/Sパターン)
上記で作製したウエハに、電子線照射装置((株)JEOL製 JBX6000FS/E;加速電圧50keV)を用いて、ウエハ上寸法がピッチ40nm、幅20nmのラインアンドスペースパターンを形成する様にEB描画のレイアウトを設計し、露光量を変えてEB露光を行った(L/Sのパターン倒れ評価用)。
(C/Hパターン)
ウエハ上寸法がピッチ60nm、ホールサイズ30nmのコンタクトホールパターンを形成する為のEB描画レイアウトを設計し、露光量を変えてEB露光を行った(C/Hのパターン倒れ評価用)。
照射後、電子線照射装置から取り出したら、ただちに、85~130℃の条件(第10表中のPEB欄参照)で60秒の条件でホットプレート上にて加熱した。
シャワー型現像装置(ACTES(株)製ADE3000S)を用いて、50回転(rpm)でウエハを回転しながら、現像液(23℃)を、200mL/分の流量で、30秒間スプレー吐出することで、現像を行った。なお、現像液としては、第8表に記載のS-1~S-20、及びSA-1~SA-9のいずれかの処理液を用いた。第10表に、各実施例及び比較例で用いた現像液を示す。
その後、50回転(rpm)でウエハを回転しながら、リンス液(23℃)を、200mL/分の流量で、15秒間スプレー吐出することで、リンス処理を行った。
最後に、2500回転(rpm)で60秒間高速回転してウエハを乾燥させた。なお、リンス液としては、第8表に記載のS-1~S-20、及びSA-1~SA-9のいずれかの処理液を用いた。第10表に、各実施例及び比較例で用いたリンス液を示す。
上述した「EUV露光評価」と同様の項目について、走査型電子顕微鏡として「S-9220」((株)日立製作所製)を用いた以外は、これと同様の方法でレジストパターンの評価を行った。結果の詳細は第10表に示す。
<ArF露光評価>
上記第5表に記載のレジスト組成物を用いて、以下の操作によりレジストパターンを形成した。
8インチシリコンウエハ上に、有機反射防止膜ARC29SR(Brewer社製)を塗布し、205℃で60秒間ベークを行い膜厚86nmの反射防止膜を形成し、その上に、上記のようにして得られた各レジスト組成物を塗布し、90~120℃の条件(第11表中のPB欄参照)で60秒間ベークし、膜厚40nmのレジスト膜を形成した。
実施例3-24~3-31、及び3-33~3-35については、上記第6表に示す上層膜形成用組成物(トップコート組成物)を上記ベーク後のレジスト膜上に塗布し、その後、下記第11表に示すPB温度(単位:℃)で60秒間に亘ってベークを行い、膜厚40nmの上層膜(トップコート)を形成した。
(L/Sパターン)
上記で作製したウエハに、ArFエキシマレーザー液浸スキャナー(ASML社製;XT1700i、NA1.20、C-Quad、アウターシグマ0.750、インナーシグマ0.650、Y偏向)を用い、線幅50nmの1:1のラインアンドスペースパターンの6%ハーフトーンマスク(スペース部分が遮蔽されている)を介して、露光量を変えて、レジスト膜のパターン露光を行った。液浸液としては超純水を用いた。その後、90~120℃の条件(第11表中のPEB欄参照)で60秒間加熱(PEB:Post Exposure Bake)した。次いで、現像装置(SOKUDO社製;RF3)を用い、下記第11表に記載の現像液(各現像液については、第8表参照のこと)で30秒間パドルして現像し、その後、50回転(rpm)でウエハを回転しながら下記第11表に記載のリンス液(各リンス液については、第8表参照のこと)で15秒間リンスし、続いて、2000rpmの回転数で30秒間ウエハを回転させることにより、ラインアンドスペースパターンを得た。
上記で作製したウエハに、ArFエキシマレーザー液浸スキャナー(ASML社製;XT1700i、NA1.20、C-Quad、アウターシグマ0.730、インナーシグマ0.630、XY偏向)を用い、ホール部分が65nmであり且つホール間のピッチが100nmである正方配列の6%ハーフトーンマスク(ホール部分が遮蔽されている)を介して、露光量を変えて、レジスト膜のパターン露光を行った。液浸液としては超純水を用いた。その後、90~120℃の条件(第11表中のPEB欄参照)で60秒間加熱(PEB:Post Exposure Bake)した。次いで、現像装置(SOKUDO社製;RF3)を用い、下記第11表に記載の現像液(各現像液については、第8表参照のこと)で30秒間パドルして現像し、その後、50回転(rpm)でウエハを回転しながら下記第11表に記載のリンス液(各リンス液については、第8表参照のこと)で15秒間リンスし、続いて、2000rpmの回転数で30秒間ウエハを回転させることにより、ホールパターンを得た。
上述した「EUV露光評価」と同様の項目について、走査型電子顕微鏡として「S-9380II」((株)日立製作所製)を用い、同様の方法でレジストパターンの評価を行った。結果の詳細は第11表に示す。
上記第9表~第11表の各実施例に示す通り、いずれの露光光源を用いた場合においても、現像液及びリンス液の少なくとも一方の処理液がSP値が16.3MPa1/2以下の第一の有機溶剤とSP値が17.1MPa1/2以上の第二の有機溶剤を含有した場合、レジストL/Sパターンにおけるパターン倒れの発生とレジストC/Hパターンにおける抜け不良の発生を同時に抑制できることがわかった。
一方、比較例から明らかなように、現像液及びリンス液のいずれもが、SP値が16.3MPa1/2以下の第一の有機溶剤とSP値が17.1MPa1/2以上の第二の有機溶剤を含有しない場合、レジストL/Sパターンにおけるパターン倒れの発生とレジストC/Hパターンにおける抜け不良の発生を同時に抑制できないことが示された。
Claims (11)
- 感活性光線又は感放射線性組成物から得られるレジスト膜に対して現像及び洗浄の少なくとも一方を行うために使用され、有機溶剤を含有するレジスト膜パターニング用の処理液であって、
SP値が16.3MPa1/2以下の第一の有機溶剤とSP値が17.1MPa1/2以上の第二の有機溶剤を含有する、処理液。 - 前記処理液が、リンス液である、請求項1に記載の処理液。
- 前記第一の有機溶剤が、炭化水素系溶剤を含む、請求項2に記載の処理液。
- 前記第一の有機溶剤が、炭素数10以上の炭化水素系溶剤を含む、請求項3に記載の処理液。
- 前記炭化水素系溶剤が、ウンデカンを含む、請求項3又は4に記載の処理液。
- 前記第二の有機溶剤が、ケトン系溶剤を含む、請求項1~5のいずれか1項に記載の処理液。
- 前記ケトン系溶剤が、非環状ケトンを含む、請求項6に記載の処理液。
- 感活性光線又は感放射線性組成物を用いてレジスト膜を形成するレジスト膜形成工程と、
前記レジスト膜を露光する露光工程と、
露光された前記レジスト膜を請求項1~7のいずれか1項に記載の処理液によって処理する処理工程と、を含む、パターン形成方法。 - 前記処理工程は、
現像液によって現像する現像工程と、
リンス液によって洗浄するリンス工程を備え、
前記リンス液が請求項1~7のいずれか1項に記載の処理液である、請求項8に記載のパターン形成方法。 - 前記現像液が、エステル系溶剤を含む、請求項9に記載のパターン形成方法。
- 前記エステル系溶剤が、酢酸ブチル、酢酸アミル、酢酸イソアミル、酢酸2-メチルブチル、酢酸1-メチルブチル、酢酸ヘキシル、プロピオン酸ペンチル、プロピオン酸ヘキシル、プロピオン酸ヘプチル、ブタン酸ブチル、及びイソブタン酸ブチルからなる群から選ばれる少なくともいずれか1種を含む溶剤である、請求項10に記載のパターン形成方法。
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JP2019212914A (ja) * | 2018-06-06 | 2019-12-12 | 東京応化工業株式会社 | 基板の処理方法及びリンス液 |
WO2020095641A1 (ja) * | 2018-11-07 | 2020-05-14 | 富士フイルム株式会社 | 感放射線性樹脂組成物、レジスト膜、パターン形成方法、電子デバイスの製造方法 |
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US11029602B2 (en) * | 2017-11-14 | 2021-06-08 | Taiwan Semiconductor Manufacturing Co., Ltd. | Photoresist composition and method of forming photoresist pattern |
US11016386B2 (en) * | 2018-06-15 | 2021-05-25 | Taiwan Semiconductor Manufacturing Co., Ltd. | Photoresist composition and method of forming photoresist pattern |
KR20240042154A (ko) * | 2018-10-03 | 2024-04-01 | 후지필름 가부시키가이샤 | 약액 및 약액 수용체 |
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